places to visit in downtown portland maine

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Welcome to Downtown Portland! At first glance you will see a historic seacoast town with a working waterfront representing Maine’s roots in a robust fishing community. But take a second look and you will also find a vibrant community of small business owners whose stores, galleries and restaurants represent the true heart of what it means to be a Mainer: hard work, fine craftsmanship and pride in representing our unique state. Maine’s largest city (but still quaint by most standards) boasts plenty of fine art, award-winning chefs and some of the best shopping experiences where you can support independent stores.

About Portland

With over 66,000 full-time residents, Portland swells to two million with the addition of its seasonal visitors and part-time residents in the summertime. The city is located on a peninsula in Casco Bay with access to many islands such as Peak’s, Great Diamond, and Long Island.

Portland stands as one of the few working waterfronts left in the United States, acting as New England’s largest tonnage seaport and second largest fishing port. Portland is also the largest foreign inbound transit tonnage port in the United States! Each year our port alone handles over 206,000 international passengers, including 41,000 cruise ship passengers.

As the economic capital of Maine, major national financial institutions as well as law firms and import/export companies base their Maine operations out of Portland. Walking through downtown Portland, you will notice modern high-rise office buildings located in historic districts intermixed with centuries old architecture.

Pick some of your favorite things to do in Portland while you visit this exciting city. To make sure that you are able to find your way around the city,  request a Guidebook  today!

Downtown Map

View/download a map of Downtown Portland.  

Downtown Neighborhoods

Portland is locally organized by neighborhoods, each with their own flavor and characteristics. Click here for a map of downtown Portland neighborhoods

Live/Work Portland

Moving to and living in Portland A diverse, creative, beautiful city, Portland offers something for almost everyone and has frequently been listed as one of America’s top cities to live, work, play and visit. Portland is a very livable city for everyone who wants to be part of a community that takes responsibility for themselves

Portland, ME   Travel Guide

Courtesy of Joe Potato Photo | Getty Images

23 Best Things to Do in Portland, Maine

Portland, Maine, is a tough little city. A large part of it burned down in the Great Fire of 1866. But in the following years, Mainers and architects and builders from nearby cities like Boston came together to rebuild using the less-flammible brick

• All Things To Do

Old Port Old Port free

U.S. News Insider Tip: Don't miss Wharf Street in Old Port, which has an eclectic mix of bars and restaurants along its pedestrian-only cobblestone street. Try Street & Co.'s upscale seafood, The Independent Ice Co.'s fine whiskeys and the Bar of Chocolate's specialty martinis and sweets. – Mariya Greeley

This downtown neighborhood is considered the city's center and bustles with things to do left and right, all the while gracefully maintaining its historical facade. The area is lined with cobblestone streets and 19th-century warehouses, and with the wharf just steps away on Commercial Street, the city's heyday as a world-renowned port town is easily felt. Tourists can benefit from ferries and cruise experiences, as well as the delectable catches aboard the lobster boats that dock there daily.

Portland, Maine, Brewery Tours Portland, Maine, Brewery Tours

U.S. News Insider Tip: For nondrinkers or those looking to take a booze break, check out places like Root Wild Kombucha and Urban Farm Fermentory . They offer a range of nonalcoholic and alcoholic drinks with atmospheres comparable to the breweries nearby. – Mariya Greeley

Beer is to Portland is what lobster is to Maine. If you visit without sampling some brew, you're missing out. Portland is considered by experts to be one of America's best beer cities thanks to its large crop of local brewers as well as its role in the microbrew movement. For a city with a population of a little more than 68,000, its nearly 20 breweries offer plenty of choices for both residents and visiting beer enthusiasts.

Portland Museum of Art Portland Museum of Art

U.S. News Insider Tip: Consider aligning your visit with a First Friday Art Walk. The first Friday evening of every month, the Arts District comes alive with art lovers taking self-guided tours of local art galleries and venues. Meanwhile, musicians, performers and artists of all types display their art in the streets. – Mariya Greeley

For such a small city, Portland houses some pretty big names in its art museum. Andy Warhol, Claude Monet and Winslow Homer are among the icons showcased within the Portland Museum of Art. Along with some of the greats, the museum features an extensive collection of American, European and contemporary works, as well as pieces from Maine artists. Paintings abound, but you'll also find photographs, sketches, pottery, furniture, ornate silverware, sculptures and so much more. With more than 18,000 pieces in its collection, visitors are bound to see something new each time they browse the museum’s galleries. Additionally, the museum hosts regular events, including movie showings, curator talks and family-focused activities.

Popular Tours

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

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Discover Portland City and Lighthouse Tour

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Downtown Portland, Maine City and Lighthouse Tour-2. 5 hour Land Tour

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Portland-area Beaches Portland-area Beaches

Maine's Atlantic beaches might be known for relatively chilly waters (peak is approximately 65 degrees Fahrenheit), even in the summer months, but Mainers will tell you how refreshing a dip in the ocean is on a hot summer day. If that doesn't sound like your idea of fun, you’ll still find plenty of activities and atmospheres to enjoy on Portland-area beaches.

Although East End Beach is the only public beach in Portland (located off Eastern Promenade ), there are more than a half-dozen others within 20 miles of downtown, each with distinct characteristics and benefits. Every summer, they’re host to families and friends laying out or playing on the sand and kayakers, sailors, surfers, paddleboarders, swimmers and more enjoying the water. Maine beaches are beautiful year-round, and ideal places for quiet walks in the offseason. 

Casco Bay Islands Casco Bay Islands

Though there is only one public beach in the town of Portland ( East End Beach ), shorelines abound in the nearby Casco Bay Islands. The Casco Bay Islands are a group of islands located off the coast of Portland, six of which are accessible by ferry year-round. Each island has its own personality, history, attractions and activities.

Cliff Island is the smallest Casco Bay Island that's accessible year-round by ferry and is home to only 60 full-time residents. All roads are unpaved here, and as such cars are seldom used. The island doesn't offer many attractions, but does provide a tranquil, secluded atmosphere.

Eastern Promenade Eastern Promenade free

Portland's waterfront is at its most picturesque at the Eastern Promenade. Beloved by locals, the Eastern Promenade is a 78-acre waterfront park located on a stretch of land separating Back Cove from the Fore River. The park offers trails, a beach, and plenty of grassy areas to simply kick back and unwind. To make the most of your visit, take a stroll along the 2-mile Eastern Promenade Trail, which starts in the heart of the Old Port .

Once an old rail line, the Eastern Promenade Trail takes visitors away from the excitement of the city's center by the rocky banks of Fort Allen Park and small yet charming East End Beach (Portland's only public beach), where you'll find plenty of locals soaking up the sun or embarking on bay adventures. To continue the coastal trek, the trail connects directly to the Back Cove Trail, which snakes for about 3.5 miles along Back Cove with picturesque views of the water and downtown skyline. There are plenty of other shorter trails and paths located in the park that bring hikers to various points of interest. Once you've gotten your fill of scenic strolls, consider a climb up the park's grassy hills for sweeping views of the bay, as well as the islands and boats that dot its deep blue waters.

Fort Williams Park Fort Williams Park free

Located adjacent to Portland Head Light in Cape Elizabeth is the 90-acre Fort Williams Park. Fort Williams was a U.S. Army fort from 1872 to 1962. A few years later, residents of Cape Elizabeth bought the land to later turn it into a park. Visitors today can picnic, tour an arboretum, hike or walk along the park's trails or visit the park's other historical sites, including Battery Keyes (one of the last batteries built on the old fort site) and Goddard Mansion (the ruins of a grand home built in the 1850s). Travelers should note there are no trash receptacles around the park so you must take your trash with you when you leave.

There's also natural and recreational amenities to explore, including tennis and pickleball courts, athletic fields and a garden designed specifically to let children explore their relationship with nature.

Portland Observatory Portland Observatory

For some of the best views of the harbor, head to the historic Portland Observatory, the country's last standing maritime signal tower. Built in 1807, the octagonal, 86-foot-tall tower was commissioned by Captain Lemuel Moody as a communication station for Portland's harbor, but it wasn't built as an altruistic measure. Moody charged ship owners an annual fee of $5 to alert merchants (who he also charged) of ships arriving. He could spot them from as far as 30 miles away with his telescope. Before the observatory was built, ships couldn't be seen from town until they came around a point of land and were practically in the harbor. Moody offered an advantage to both paying captains and merchants, while also making a tidy profit for himself.

Eventually, the two-way radio replaced the tower's function, but the Moody family operated the tower until 1923. After some years of neglect the observatory was donated to Portland and in 1984, Greater Portland Landmarks took over and restored it. Recent visitors said the views from the observatory are not-to-be missed and its history is fascinating. Reviewers also advise allowing 45 minutes for the observatory tour. There is no elevator, so you'll have to climb the stairs to the top to take in the views, but past travelers say the pace is manageable.

Portland Tall Ship Cruise on Casco Bay

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Vintage Fire Truck Sightseeing Tour of Portland Maine

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Harbor Lights and Sights Cruise

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Victoria Mansion (Morse-Libby House) Victoria Mansion (Morse-Libby House)

Architecture buffs and lovers of interior design will be swept up by the opulence of the Victoria Mansion (aka the Morse-Libby House or Morse-Libby Mansion). This National Historic Landmark was originally built in the mid-1800s as a summer house for hotelier Ruggles Sylvester Morse. In 1940, William Holmes, a New York educator visiting Portland, purchased the home. He and his sister (an interior design instructor) turned it into a museum named in honor of Queen Victoria.

What makes the Victoria Mansion so important in the eyes of historians is that it's seen as an exemplary illustration of pre-Civil War grandeur. The exterior of the house was modeled after an Italian villa and features an ornate square tower, numerous balconies and piazzas. Inside, prepare to be even more amazed. Ninety percent of the original interiors are still intact, with carved wood paneled walls, gas light fixtures, cherub-clad crown molds, and ornate draperies and carpeting throughout. Designed by Gustave Herter of Herter Brothers, one of the most popular design firms of the day, it is the only work of his kind in the U.S. that remains intact.

Peaks Island Peaks Island free

Portland doesn't end at the waterfront. Peaks Island, one of the Casco Bay Islands , is 3 miles east of downtown's shore and about a 15-minute boat ride away. Peaks Island was known as the Coney Island of Maine in the 19th century (it was home to amusement parks, theaters and more), but nowadays it feels more like a quaint neighborhood with roughly 1,000 year-round residents.

Peaks is a perfect low-key day trip for history buffs, art lovers and outdoor enthusiasts. When you arrive, rent a bike or golf cart, the preferred modes of transportation on the island. Head to Baba's Cafe, Inn on Peaks or Island Lobster Company to fuel up for the day while overlooking the ocean. From there, explore the galleries and shops along the harbor side. Cool off at Sandy Beach or trek the nearly 4-mile loop trail that takes you around the island, passing scenic views and the remnants of historic Battery Steele — an important coastal defense battery constructed during World War II to protect the entrance to Casco Bay. For more Peaks Island history, stop by Fifth Maine Museum, or for something playful head to the world's only Umbrella Cover Museum, a quirky collection that is dedicated to the appreciation of the mundane.

Hadlock Field Hadlock Field

U.S. News Insider Tip: Special activities, like fireworks or "Bark in the Park" games, which allow you to bring a four-legged friend and sit in a designated pets area, make the experience extra special. Look for them when booking tickets. – Mariya Greeley

For Portland pride, look no further than Hadlock Field. In the summer, the field hosts regular games for the beloved Portland Sea Dogs, the local minor league baseball team. The field was named after Edson Hadlock Jr., who coached baseball at Portland High School from 1950 to 1978.

Portland Head Light Portland Head Light

Commissioned by George Washington in 1787, this lighthouse project was provided $750 by the General Court of Massachusetts when Maine was still a part of Massachusetts. When the U.S. government took control in 1790, the lighthouse was given an additional $1,500 for its completion. The lighthouse got its name from being situated at the entrance for ships at Portland Harbor. Portland Head Light was first lit in 1791, making it the oldest lighthouse in Maine.

Located about 5 miles southeast of Portland in Cape Elizabeth's Fort Williams Park , the tower provided navigation to ships for almost 200 years. The lighthouse was decommissioned by the U.S. Coast Guard in 1989 when it became an automated tower.

The Holy Donut The Holy Donut

In 2010, Leigh Kellis felt the Portland food scene was missing great doughnuts. So she decided to make them. After months of experimenting with different recipes in her kitchen on Portland's Munjoy Hill , Kellis landed on a mix that met her standards. Her variation on a northern Maine recipe included a type of food you might not expect in doughnuts: potatoes. Riced potatoes added a unique flavor, texture and consistency that set Kellis' doughnuts apart, and orders from local shops started coming in. With her family's support, Kellis soon opened the first Holy Donut retail location. Now, the family-owned business is a bonafide doughnut destination with four Maine locations: two in Portland, one in Scarborough and one in Arundel.

With about 20 rotating imaginative doughnut flavors – including seasonal, gluten-free and vegan options – you have a good chance of finding a flavor that you'll love. Though potato doughnuts aren't for everyone, many recent customers rave about unique flavors like dark chocolate sea salt, maple bacon and pomegranate. They describe the doughnuts as dense, filling and delicious. Reviewers also tend to mention the friendly service adding to their positive experiences.

Scenic Lighthouse Boat Cruise from Portland's Old Port

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Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

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Portland, Maine: Hidden Histories Guided Walking Tour

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Two Lights Lighthouses Two Lights Lighthouses free

Built in 1828, these two Cape Elizabeth lighthouses were the first twin lighthouses on the coast of Maine. They may look familiar: One of them was featured in Edward Hopper's well-known "The Lighthouse at Two Lights," a painting housed in the  Metropolitan Museum of Art in New York City . Today, the eastern lighthouse on Lighthouse Point Road is an active, automated station, shining 17 miles out to sea, while the western lighthouse is a private residence. Neither lighthouse is open to the public.

You can still get lighthouse views at On the Rocks at Two Lights, a lookout at Dyer Cove where recent visitors praised the natural beauty and recommend sunrise and sunset trips. While you’re there, stop for a bite at the Lobster Shack at Two Lights, a seasonal award-winning restaurant that dates back to the 1920s. The area is 6 miles south of Portland Head Light if you're in the mood for a lighthouse road trip.

Wadsworth-Longfellow House Wadsworth-Longfellow House

Built after the Revolutionary War, the Wadsworth-Longfellow House was home to four generations of the esteemed family whose contributions to American culture are now celebrated in this museum. The most famous person in this family was 19th-century poet Henry Wadsworth Longfellow, who grew up in the home.

Along with its esteemed namesake, the home is also important to Portland and U.S. history. The building is the oldest standing structure on the Portland peninsula, the first brick dwelling in the area and the first home museum in Maine. The site is operated by the Maine Historical Society.

Children's Museum and Theatre of Maine Children's Museum and Theatre of Maine

U.S. News Insider tip: Children's Museum and Theatre of Maine is next to Thompson's Point, a venue that hosts big name music acts for outdoor concerts and weekly events during the summer. The museum is also steps from the International Cryptozoology Museum where you can explore BigFoot mythology and more. – Mariya Greeley

If you're looking for something to do with the kids in Portland, the Children's Museum and Theatre of Maine is a must-see attraction. With more than 30,000 square feet of space, this museum provides interactive learning and fun for the entire family.

Coastal Maine Botanical Gardens Coastal Maine Botanical Gardens

U.S. News Insider Tip: Visiting during the holiday season? The garden creates a mile of spectacular light displays , called Gardens Aglow, open a few nights a week to brighten the winter darkness. – Mariya Greeley

The Coastal Maine Botanical Gardens is an attraction that took 16 years to create. What started as a dream for a public garden became the largest botanical garden in New England. Located about 60 miles northeast of Portland, the gardens consist of more than 300 acres of land, 17 of which feature plants native to the state. Each garden at the facility has a specific theme, including dahlias, bees and rhododendron, among others.

Munjoy Hill Munjoy Hill free

U.S. News Insider Tip: Munjoy Hill's Duckfat Frites Shack, a little sister location to downtown's Duckfat, has a limited menu, but shorter wait times than its popular sibling. You'll find the order window down an alley beside Oxbow Blending & Bottling. – Mariya Greeley

If someone mentions happenings on "the Hill" in Portland, they're likely not referring to Washington, D.C. politics but to the Munjoy Hill neighborhood of the city. Munjoy Hill is Portland's easternmost neighborhood and lies between Washington Avenue and Mountfort Street on one side and Casco Bay on the three others.

A Walk Through Time Tour in Portland

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Sunset Lighthouse Harbor Cruise from Portland's Old Port

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Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

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Tate House Museum Tate House Museum

Tate House was built in 1755 for Captain George Tate and his family. Tate was a senior mast agent for the British Royal Navy, a role which meant he was responsible for the transport of white pines — now Maine’s state tree — from Maine to England. During hourly site tours, visitors should expect to see artifacts, furnishings and the grounds, which not only tell the story of how the Tate family lived in the 18th century, but also the importance of mast trade during this period.

Located about 4 miles west of downtown, the Tate House is the only pre-Revolutionary home in Portland that is open to the public. Past visitors say that the tour is an educational experience.

Portland Fire Engine Co. Tour Portland Fire Engine Co. Tour

Looking for a unique way to explore Portland? The Portland Fire Engine Co. sightseeing tour takes travelers on a ride around town in a vintage fire truck.

Expect to see scenic coastal views of Portland, along with historical sights, lighthouses and Civil War forts. During the 50-minute tour, you'll also enjoy a live narration of Portland history and view historical images provided by the Maine Historical Society on the truck's LED TV. Past tourgoers describe this as a fun outing and applaud the insightful guides.

Maine Narrow Gauge Railroad Co. and Museum Maine Narrow Gauge Railroad Co. and Museum

U.S. News Insider Tip: Look out for special events like Ice Cream Trains and Sunset Express rides on weekend evenings during the warmer months and special "Polar Express" rides during the holiday season. – Mariya Greeley

Located about 1.5 miles from the Portland Museum of Art , the Maine Narrow Gauge Railroad Co. and Museum teaches travelers about train preservation and Maine's narrow gauge railway history. The state's two-foot gauge railway system was made of tracks less than half the width of standard gauge railways. These narrow tracks were cheaper and easier to build while allowing trains to navigate Maine’s tough terrain of forests, rocky hills and mountains. A unique system, these rails helped to connect rural areas with larger cities and made travel and transportation of goods more accessible. From the 1870s until the 1940s, about 200 miles of narrow gauge railroads served many small communities in Maine.

Palace Playland Palace Playland

Situated about 20 miles south of Portland in the town of Old Orchard Beach, this 5-acre amusement park is New England's only beachfront amusement park. Past visitors say Palace Playland is an awesome place to take the family.

The park has a 24,000-square-foot arcade and features more than 200 games like Skee Ball and air hockey. And no amusement park would be complete without rides. Younger visitors can enjoy kiddie rides like a carousel and spinning tea cups, while older kids and adults test their bravery on the park's thrill rides like the Sea Viper roller coaster.

Funtown Splashtown USA Funtown Splashtown USA

Located about 15 miles south of Portland in Saco, Maine, Funtown Splashtown USA is a family-owned amusement park. The park is home to about 50 rides, water slides, pools and games for travelers to enjoy. Past visitors said the park is particularly fun for families with a variety of rides and clean facilities. However, some caution that lines can be quite long depending on the day and on-site food can be pricey.

Standout rides include Excalibur, Maine's only wooden roller coaster, and the Thunder Falls Log Flume, the longest and tallest log flume ride in Maine. The facility has several water slides, rides and pools at its Splashtown Water Park. And when your stomach starts to rumble, there are a variety of different eateries on-site (outside food and drinks are also allowed). 

Donut Tasting Walking Tour in Portland’s Old Port

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Guided RIB Boat Adventure of Casco Bay

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Sunset Sea Kayak Tour of Casco Bay

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Portland Maine Bucket List: 15 Cool Things to Do

From mouth-watering restaurants to epic lighthouses to a booming craft brew scene, Maine’s main coastal city of Portland just may have it all. It’s casual, yet trendy. It’s impressive, yet doesn’t try too hard. It is a city of many layers—it’s a seaport, historical hub and cultural hotspot all rolled into one.

No matter what you come here for, or when you arrive, the list of things to do in Portland is pleasantly long. Here is a guide to what to see and the best ways to explore the city.

The Best Attractions & Things to Do in Portland, Maine

1. ✦  eat a holy donut.

There could not be a better name than Holy Donut for this establishment as the taste of their specialty donuts is simply divine. Created with real Maine potatoes mixed with wheat flour, the donuts are made fresh with all-natural ingredients.

You can go to any of their three locations–Park Avenue, Exchange Street and Scarborough–for your dose of donuts. There’s almost always a line out the door, so for the best selections arrive right at opening!

Of course, everyone will have their favorite flavors of the 18 different ones offered, but a clear frontrunner is the Dark Chocolate with Sea Salt, followed by the Maple Bacon, Fresh Lemon and Toasted Coconut. Mmm!

2. ✦  Take the Ferry to Peaks Island

A 20-minute journey from Portland via the Casco Bay Lines ferry will have you end up on Peaks Island where the laidback lifestyle will surely encompass you. The quaint island has a population of under 1,000, but it is packed with something for everyone. Spend your time here eating fresh seafood at one of the local cafes, relaxing on one of the many beautiful beachfronts or renting a golf cart to tour the entire island’s attractions, like the World War II history museum.

If you are up for a little more activity, opt to pop into a kayak to tool around the bay or take a bike ride along the scenic pathways. Whatever you do, don’t miss the quirky Umbrella Cover Museum with its assortment of umbrella covers displayed with various themes (including an X-rated section!).

3. ✦  Spend an Afternoon at the Old Port

Cobblestone streets, red-bricked buildings, charming boutiques, trendy restaurants and fishing piers—that’s what you’ll find in Portland’s Old Port. It’s a quaint historic district that overlooks the Fore River. Many folks head there in early June for the Old Port Festival or in December for Merry Madness. But, it is fun to explore anytime of the year!

If you are a fashionista, don’t miss a stop by Rough & Tumble to ogle their handmade handbags, Aristelle for some luxurious intimate apparel and Zane that has a beautifully curated collection of designer labels.

The shopping scene can get overwhelming in Portland, but In the Know Shopping can take you on a tour to many of their favorites.

For all the home chefs out there, don’t miss a stop at Salt Cellar who carries a full line of gourmet flavors, or pop into Skordo who specializes in freshly ground spices, herbs, blends and rubs.

For eats, grab some thoughtful small plates at Central Provisions or indulge in the chef’s tasting menu at Miyake. And if you are a French fries lover like myself, you have to book a seat at Duck Fat . Or just take a culinary walking tour in Old Port to get a sampling of local food. 

4. ✦  Sail the Casco Bay with Calendar Islands Sailing

Can you just imagine basking in the sun onboard a beautiful sailing boat with the wind in your hair and a glass of champagne in your hand? You don’t have to, because this can be your reality.  There’s no better bucket list worthy way to explore Casco Bay and its islands than on a sailing trip, and I had an incredible time doing so with Calendar Islands Sailing Co.

One of the most popular tours is their two-hour coastal sightseeing excursion, but they also offer island-to-island day cruises or personally customized trips. If you are up for more of an experience than opt for one of their overnight adventures. Either way, you will get a chance to discover the breath-taking scenery of the coast, the sights along the way and the islands.

Secrets of Casco Bay from GLP Films on Vimeo .

5. ✦  see the lighthouses.

If you are the kind who just can’t resist historical lighthouses there a handful in the Portland area, each with its own charm. The Portland Breakwater Lighthouse (aka: Bug Light) is a small lighthouse that sits at the end of the breaker and is unique because it was designed to look like a 4 th century Greek monument.

Built in 1897, Spring Point Ledge Lighthouse is a caisson-style light station (the only one in the United States!), but what is special about this one is that you have the opportunity to tour it. But, the most impressive and the one that is best known is the Portland Head Light at Fort Williams Park. You can easily spend a couple of hours strolling along the pathways to check out Maine’s oldest lighthouse from every angle. For even more information read our article: 5 Epic Lighthouses in (& Around) Portland Maine

For an extra bucket list worthy experience try taking the Lighthouse Bike Tour that will take you to three lighthouses, and includes a lobster roll! 

6. ✦  Visit the Historic Victoria Mansion

Built around 1860, this ornate summer mansion turned museum is impressive with its vintage look and captivating history. Everything about it is grand including the exterior that has balconies and verandas, and an interior décor of gilded areas, wall paintings, stained-glass skylight, beautiful draperies and splendid furniture.

Take a tour inside with knowledgeable guides who will tell you all about the mansion–from its origins as a summer residence for hotelier Ruggles Sylvester Morse to being bought by a resident of Maine who converted it into a museum. For its time, the mansion also had modern amenities such as hot and cold water and a central heating system.

7. ✧  Explore Maine’s Historic Eastern Cemetery

This is not your typical activity for any itinerary, but when a cemetery has a long and riveting history, it makes for an interesting visit as is the case with Eastern Cemetery. Dating back to 1668, this cemetery with thousands of graves is a chronicle of the life and times of several people including Portland’s leaders and soldiers. It also offers a glimpse into the social divisions of the early times as the graves are divided into different locations.

You can venture there on your own or opt for a guided tour organized by the non-profit group Spirits Alive from June to October.

8. ✦  Go on a Food tour

‘Live to eat’ should be your motto while in Portland as it has a vast variety of yummy food options and restaurants. You can easily set out to find your own delicious meal (which won’t be hard!) or unleash your inner foodie while learning about sustainability on a guided Maine Food for Thought tour.

The educational food tour will lead you on a walking path to eat your way through restaurants who feature locally sourced ingredients and a farm-to-table mindset. You will also get an understanding of the local food culture and delve even deeper with the stories behind the plate.

Though the stops and dishes can change, there was quite a delectable sampling on the day of my tour. For instance, the Union Restaurant dished up a bowl of locally sourced clam chowder with trout and Evo served a beet salad with a kalamata olive crumble and famous Maine blueberries. All the other stops were equally as delicious.

I can promise you that you will not leave this tour disappointed or hungry!

Take a peek behind-the-scenes:

GLP Films on Vimeo .

9. ✧  visit the portland observatory.

An imposing seven-story structure, the Portland Observatory is the only maritime signal tower still standing in America. Back when it was built by Captain Lemuel Moody in 1807, it functioned as a communication tower for ships making their way to the docks. You can go on guided tours of this octagonal tower that stays open from late May to October.

Each floor has interesting displays related to Portland history, maritime traditions and the observatory. You can climb to the top of the tower’s lantern (cupola) and then arriving at the lantern’s balcony will reward you with tremendous 360-degree views over Portland and the bay.

10. ✦  Enjoy the Craft Beer Scene

For all you beer lovers out there, Portland’s craft beer scene is booming! There’s nothing quite like drinking a ‘cold one’ in the open air while sitting at a picnic table with your pooch or playing a game of corn hole. Right? With a booming craft beer scene there is no shortage of good breweries to choose from.

Bunker Brewing Company is set inside a 1920s garage whose doors slide wide open. Novare Res Bier Café is a popular hidden beer garden that not only has a great food menu but also a nice international draft and bottle list. Of course, you can’t forget a visit to Allagash Brewery where you can take a classic tour then plop on their patio to indulge.

For a little more unique beer experience, pop onto a tour with the Maine Brew Bus whose expert guides (and bright green bus) will take you on a trip to discover the distilleries, breweries and wineries in the area. If being on a bus is not your thing, then take a walking beer tasting tour .

11. ✧  Visit the Portland Museum of Art

If your perfect afternoon includes ogling famous works of art, then the Portland Museum of Art is one of the top things for you to do in the city. With a collection of over 18,000 pieces on rotation you are bound to see some notable names during your visit, like Claude Monet and Andy Warhol. But, that’s not all! Ranging from paintings to pottery and sketches to sculptures, the exhibits include American, European and even local Maine works.

12. ✦  Get Fries at Duckfat Friteshack

Do you love French fries as much as me? Then don’t walk, run to Duckfat Friteshack for some of the best made from hand-cut Maine potatoes and fried in—you guessed it— duck fat. The Friteshack is an offshoot of the well-known Duckfat restaurant in Portland, and a popular one at that.

The shack is a casual joint where you place your order at the walk-up window from the limited menu. Fries can totally be a meal (especially if they are in the form of duck poutine), but in case you need more add on some doughnut holes or an extra thick milkshake.

Tip: Though I deemed the truffle ketchup the best homemade dipping sauce they serve, you can order a flight of all the six and judge for yourself.

13. ✦  Shop for Sea Bags

If you want to take home the ultimate Maine souvenir then don’t miss a stop at Sea Bags , where nautically inspired totes are made from recycled sails cloth. No two bags have the exact same markings! The magic happens in the heart of a working waterfront, where craftspeople meticulously design, sew and finish each piece.

You can shop right there in the front storeroom where hundreds are displayed, including their vintage collection that feature mainsail insignia logos. As each bag is unique, leave yourself some time to pick out the perfect one for you.

14. ✦  Drink at a Secret Speakeasy

Before you actually get to drink at Lincoln’s, you’ll have to find it first, and know how to get in—two minor details that won’t be shared here. But, that’s half the fun! Once you’ve cracked the code to get into this chill underground bar you’ll be greeted with a packed house who have come for the low-key vibe and $5 drinks. Yep, all the drinks are just five bucks, hence the name. Get it?

15. ✦  Eat Lots of Lobster

It doesn’t get more quintessential Maine then eating fresh lobster, and Portland has some of the best. You can start the indulgence with the well-known lobster roll. Typically, the famous rolls are simply made with fresh chunks of lobster meat, melted butter (and/or mayonnaise) served on a top-split New England hot dog roll. If you don’t want the carbs, then just opt for a whole lobster tail on a plate. You don’t have to complicate things to make them delicious!

There are plenty of places to get your lobster fix. Luke’s is one of the favorites amongst the tourists, but many of the locals also swear by Bob’s Clam Hut or Porthole . Warning: you may just have to do a lot of research (lobster sampling) to find your favorite.

A peek at where Maine’s lobster comes from:

Pete the Lobsterman from GLP Films on Vimeo

From lobster to museums to a booming craft beer scene, the city of Portland is packed with the best things to do and attractions to see. Be it on the water or on land, Maine’s hub is the perfect blend of the best activities.

Essential Tips for Visiting Portland, Maine Getting There: Portland International Jetport is a major hub and most airlines will fly into it. You can easily check for the best fare deals at Skyscanner , which also has the option to choose ‘cheapest month’ as the departure to find the lowest priced dates to fly to your destination. From the airport to the city center, you can use the subway, private car, limousine, shuttle or take a taxi. Where to Stay in Portland, Maine: It’s best to stay near the city center, public transportation or the area that you will be spending the most time in. AC Hotel by Marriott is a great choice in the Portland district. For something on the less expensive side, try Inn at St John located in Portland. For a hotel with a little more extravagance, book a room at the Blind Tiger Guest House . Or search some great deals on hotels of your choice at Booking.com . If you’re looking for more of a home atmosphere (or are traveling with a group of people), head over to Airbnb that has houses, apartments and even just a room for rent in every price range.  Getting Around: Driving in a new destination can be a bit of a challenge, but if you choose to rent a car, RentalCars.com has great deals. If you are not renting a car, there are plenty of other options. Taxis, Lyft and Uber are available all over the city. For a more budget friendly option, you can take the public bus or metro/subway. The DiriGo Pass Card is an all-in-one transit card offering rides on multiple forms of transportation (metro, train, bus) for one fee. Best Tours in Portland, Maine : You can find some of the top tours at Get Your Guide or Viator , and here are some of the top ones. tours: Portland: Old Port Culinary Walking Tour Portland, Maine: 2-Hour History Tour with Sweet Treat The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local Insurance: It’s always a good idea to travel fully insured so you are protected in case of trip cancellations or medical emergencies. You can check out pricing at Travelex Insurance . This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. For more information read my full disclosure .

More About Maine

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10 thoughts on “Portland Maine Bucket List: 15 Cool Things to Do”

Will be coming in September

I’m sure you will love it there!

We’re coming in October can’t wait to have lobster.

Thanks for the info, now we have to make choices! Smooches!

We’re heading up this weekend and next week will try some of your suggestions!

Awesome list! We are here for the next 2 days and will try to cram in as much of these as possible!

I will be on a tour in Oct. 2022 So this will come in handy. I

That’s exciting. Enjoy!

Love this bucket list for Portland, Maine! I’ve been wanting to visit for years and this has given me some great ideas for things to do. The lobster fishing tour and exploring the Old Port are definitely at the top of my list. Can’t wait to try some of the delicious food and drinks, and maybe even spot some puffins!

I’m glad you enjoyed the bucket list for Portland, Maine! Your enthusiasm is contagious, and I’m sure you’ll have an amazing time exploring the Old Port and going on the lobster fishing tour. The food and drinks are indeed a highlight, so be prepared for some delicious experiences. And spotting puffins would be such a fantastic bonus! Safe travels and have a wonderful adventure in Portland. If you ever need more recommendations or have questions along the way, feel free to reach out. Enjoy every moment of your trip!

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Downtown Portland

The Longfellow House and Garden

Longfellow was born in Portland in 1807, he became a national literary figure by the 1850s. Visit his home and garden, an urban oasis!

Grab a sandwich on Congress Street and head to the Olmstead designed Deering Oaks Park for an afternoon picnic.

Check out the Portland Farmer's Market Voted Top Ten Market in the US by Travel and Leisure Magazine Wednesdays - Congress Square Saturdays - Deering Park

Tour the Tate House and Colonial Garden in Portland

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The Ultimate Guide to the 59 Best Things to Do in Portland, Maine

The Definitive Handbook to Portland, Maine: Uncovering 59 Must-Experience Activities in the City

Looking for things to do in Portland, Maine? I’ve got you covered. From lighthouses to breweries, here are the top 59 experiences in this charming coastal town.

I visited Portland in October and I completely fell in love with this little coastal town. I found myself exploring every nook and cranny as much as I could. And guess what? For a small town, it turns out that there is a lot to do in Portland, Maine.

Between exploring breathtaking natural beauty, strolling down historic streets, and checking out cultural landmarks, there is something for everyone here. But you’d hardly know it since most of Portland’s awesome activities are hardly ever talked about!

So, if you’re visiting Portland and looking for some fun things to do, you’re in the right place. From diving into culture and history at museums, taste testing at the many breweries, and exploring Portland’s famous lighthouses, I’m going to go over the 59 very best things to do in Portland, Maine.

Top Experiences in Portland, Maine

⭐ Donut Tasting Walking Tour in Portland’s Old Port

🌟 Old Port Culinary Walking Tour

⭐ A Walk Through Time Tour in Portland

🌟 Stand-Up Paddle Sunset Tour in Portland

Explore the Historic Old Port District

See the lighthouses, indulge in culinary delights, quench your thirst at portland’s bars, breweries, and speakeasies, enjoy outdoor activities, learn something new at portland’s museums, experience portland’s arts and culture, see portland in a new way with a unique tour, the cozy bnb, public transportation, 10 essential packing items you’ll need for portland, maine, is portland, maine worth visiting, is portland, maine, worth a day trip, how much time do you need in portland, maine, when is the best time to visit portland, maine, can you do a day trip to acadia national park from portland, maine, what to do in portland, maine, when it rains, how to explore nearby towns and attractions, final thoughts on what to do in portland, maine, 59 best things to do in portland, maine.

Discover Portland, Maine’s authentic charm through the 59 best things to do in Portland, Maine. 

Portland’s Old Port is a charming blend of cobblestone streets, 19th-century brick buildings housing posh boutiques and art galleries, and renowned restaurants and bars. Whether you’re visiting Portland in the summer, winter, spring, or fall, this historic neighborhood is a must-stop location.

1. Portland Freedom Trail

Explore the Portland Freedom Trail. It’s a free and self-guided tour highlighting 13 significant sites commemorating 19th-century Black Mainers who played pivotal roles in the fight against slavery.

The trail unveils the local Underground Railroad’s clandestine routes. As you go from milestone to milestone, you’ll wander through historic wharves, churches, private homes with hidden passageways, and businesses that ingeniously distributed anti-slavery pamphlets alongside their products. 

This immersive experience sheds light on the incredible journey of formerly enslaved individuals seeking freedom in Maine and Canada.

This is an awesome free activity in Portland.

Best for: history enthusiasts, cultural explorers, and those interested in the abolitionist movement. Location: Start anywhere on the trail’s 2-mile trek, such as Maine State Pier or Lincoln Park.

2. Shop til you drop on Exchange Street

One of the best things about exploring a historic town is wandering through the many shops and boutiques in the city’s downtown area. Portland does not disappoint when it comes to charming little stores featuring unique souvenirs that are so tempting to purchase and take home. I myself ended up with a pair of jade and raccoon teeth earrings (I made sure they were ethically sourced) from the Maine Souvenir Shop. 

Indulge in a shopping extravaganza on Exchange Street in Old Port, Portland. Lined with eclectic boutiques, this vibrant street invites you to discover unique treasures, from fashion finds to locally crafted art. 

Best for: travelers who relish eclectic finds and locally crafted treasures. Location: Start on the corner of Congress Street and Exchange Street and make your way down to Commercial Street (as well as the rest of the Old Port area).

3. A Walk Through Time Tour in Portland

A Walk Through Time Tour is a mesmerizing exploration of Portland’s rich history. Our tour was led by a seasoned local guide named James who has been living in Portland for 30 years.

This immersive walking tour weaves tales of Portland’s past as you traverse the Old Port, downtown, and waterfront areas. 

Highlights include exclusive access to the Customs House, glimpses into historic sites like Hendry Wadsworth-Longfellow’s home, and engaging narratives about Portland’s fascinating history.

➡️ To see my detailed review of my experience on the A Walk Through Time Tour in Portland, Click Here.

Best for: history enthusiasts seeking an immersive and personalized exploration led by a seasoned local guide. Location: You’ll meet at a designated meeting spot on Commercial Street and then tour much of Portland’s downtown area.

4. Audio Guided Walking Tour from Old Port of Portland, Maine

Explore Portland, Maine, at your own pace with the Audio Guided Walking Tour from Old Port . 

This self-paced adventure offers the freedom to discover the city’s historic streets on your schedule. With professionally produced narration and music accessible on your smartphone, immerse yourself in captivating tales of landmarks like cobblestone streets, Wharf Street, and Henry Wadsworth Longfellow’s home. 

Uncover diverse histories, from lighthouses to prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, and colonial times. 

The tour never expires, providing a comprehensive guide for every visit to this coastal town. With this experience, you’ll always have an immersive adventure waiting for you in Portland.

Best for: independent travelers who prefer a self-paced experience. Location: Portland, Maine

5. Stroll Through Commerical Street

Stroll through Commercial Street in Old Port, Portland, Maine, where the salty breeze mingles with the smell of fresh salt air. Cobblestone streets lead you past an array of charming boutiques, art galleries, and 19th-century brick buildings that encapsulate the neighborhood’s cool and quaint atmosphere. 

Explore world-famous restaurants, sip coffee at cozy cafes, and witness the vibrant working harbor. 

In summer, the street buzzes with tourists exploring shops and sailing with the Portland Schooner Co. (more on them later), while fall and winter offer a more intimate experience, drawing locals out to enjoy the serene charm of this waterfront gem.

Best for: cultural explorers, history buffs, food enthusiasts, and those simply looking to soak in the charming atmosphere of Old Port, Portland, Maine. Location: Start at the corner of Franklin Street and Commercial Street by the Standard Baking Co. and make your way west through the Old Port.

6. See the first chewing gum factory at the Hub Furniture building

Stroll past the Hub Furniture building while blowing a bubble. While this building is now the home to Hub Furniture, 200 years ago, it was the place where John Bacon Curtis opened up the first-ever chewing gum factory and popularized the treat with the American audience.

Best For: History and chewing gum enthusiasts. Location: 291 Fore Street

➡️ Click here to learn about the best walking tours in the Historic Old Port District!

The crown jewel of Portland is its beautiful lighthouses. No trip to this coastal city is complete without visiting at least one if not all five.

Another fantastic thing about visiting the lighthouses? It’s free! Except for paying for parking in a few locations or entering optional museums, the Portland lighthouses are free to visit.

7. Portland Head Light (and Ram Island Ledge Light)

Portland Head Light is Maine’s oldest lighthouse dating back to 1791 and was commissioned by George Washington. Nestled in Fort Williams Park, its iconic tower offers panoramic views of the rugged coastline and the Atlantic. 

The former keeper’s quarters house a historic museum, inviting visitors to delve into centuries of maritime heritage. Whether exploring the 90-acre park or standing at the lighthouse’s base, every angle presents a photographer’s paradise. 

From this lighthouse, you can see nearly all the other lighthouses in the Portland area, including the Ram Island Ledge Light which is situated on an island out at sea and not accessible unless you take a boat or kayaking tour.

Best for: visitors who appreciate historical landmarks, maritime history, and breathtaking coastal landscapes. Location: Fort Williams Park, Cape Elizabeth, ME 04107

8. Two Lights State Park/Cape Elizabeth Lights

Two Lights State Park, home to Maine’s first twin lighthouses commissioned in 1828, offers charming coastal views on its 41-acre grounds. Although the lighthouses are not accessible to the public, visitors can enjoy scenic trails while picnicking and watching sunsets. One of the lights, still operational, adds a magical touch to evenings. 

Best for: Visitors who appreciate scenic trails, picnics, and sunset views against the backdrop of historic twin lighthouses. Location: 7 Tower Dr, Cape Elizabeth, ME 04107

9. Portland Breakwater Lighthouse (Bug Light Park)

Bug Light, aptly named for its small size, is a charming stop for maritime enthusiasts in Bug Light Park. 

This lighthouse, surrounded by greenery and framing the Atlantic Ocean, provides a unique view of Portland Harbor. Originally constructed in 1855 as a wooden structure, it was later moved and rebuilt in 1875 during the extension of the breakwater. 

Its quaint allure, combined with its proximity to the city, makes Bug Light an easily accessible gem for visitors seeking a delightful and historic maritime experience.

Best for: maritime enthusiasts and those seeking a charming, easily accessible gem near Portland. Location: S Portland Greenbelt Pathway, Bug Light Park, South Portland, ME 04106

10. Spring Point Ledge Lighthouse

Perched on a stone breakwater extending into Portland Harbor, Spring Point Ledge Lighthouse, completed in 1897, is a captivating structure accessible by a scenic walk. Its unique location against the ocean makes it a photographer’s favorite and the caisson foundation showcases innovative engineering. 

Walking across the breakwater to reach the lighthouse’s base is a quick yet adventurous stroll, providing a memorable experience amid the scenic beauty of Portland Harbor.

Best for: photography enthusiasts and those seeking a brief yet adventurous stroll on a scenic breakwater. Location: 2 Fort Rd, South Portland, ME 04106; located on the Southern Maine Community College Campus

➡️ To learn more about the lighthouses of Portland, use my Portland, Maine Lighthouse Guide!

When thinking about the cities with the best food in the USA, a foodie’s mind usually turns to one of two coastal cities: Portland or San Fransisco. 

While I can’t speak to the delicacies hidden inside of good ol’ San Fran, I can tell you about some of the best places to eat in Portland, Maine.

11. The Holy Donut

In 2010, sensing a gap in Portland’s culinary scene, Leigh Kellis embarked on a doughnut-making journey from her Munjoy Hill kitchen, incorporating a surprising ingredient: potatoes. The unique blend, inspired by a northern Maine recipe, yielded distinctive flavors and textures, leading to the birth of Holy Donut. 

With family support, Kellis opened the first retail location, and the family-owned business has since expanded to four Maine locations. 

Offering around 20 innovative flavors, including seasonal, gluten-free, and vegan options, Holy Donut has become a sought-after doughnut destination, praised for its dense, delicious creations and friendly service. 

Arrive early for the freshest selection, as each location opens between 6 and 7 a.m. But don’t wait too long, the store closes when they sell out.

Best for: those seeking unique culinary experiences. Location: 177 Commercial St, Portland, ME 04101

12. Standard Baking Co.

Discover the essence of European baking at Standard Baking Co., a cherished Portland, Maine bakery founded in 1995 by Alison Pray and Matt James. The journey started with a single French baguette in 1995, and today, with over 15 dedicated staff, the bakery on Commercial Street thrives. 

Committed to quality, Standard Baking Co. meticulously sources organic and local ingredients, ensuring every baked good is crafted with love. Immerse yourself in the tradition of exceptional baking at this beloved local gem.

Best for: bread lovers who love traditional craftsmanship made with organic ingredients. Location: 75 Commercial St, Portland, ME 04101

13. Donut Tasting Walking Tour in Portland’s Old Port

The Sweet Delights Donut Tasting Walking Tour in Portland’s Old Port will have you wandering the streets and indulging your sweet tooth with six unique donut samples from three renowned donut shops. 

This family-friendly adventure offers culinary exploration, historical insight into Maine’s donut creation legend, and exclusive access to The Holy Donut.

Best for: donut lovers and sweet tooths. Location: 2 Exchange St, Portland, ME 04101, USA

14. Green Elephant

An exceptional place for your lunch stop, experience culinary balance at the Green Elephant Vegetarian Bistro. It’s Portland’s haven for mindful dining since 2007. Founded by Chef Dan Sriprasert, the restaurant fuses Thai roots with diverse Asian influences, creating a meat-free menu for all. 

The Green Elephant sources local products, offering an array of Portland beers, home-grown teas, and a superb wine list. Join them for Asian-inspired vegetarian cuisine made with love.

Best for: vegans, vegetarians, and mindful eaters. Location: 608 Congress St, Portland, ME 04101

15. Old Port Culinary Walking Tour from Portland

Immerse yourself in Portland’s culinary scene with the Old Port Culinary Walking Tour , a foodie’s delight in the heart of historic Old Port. Led by an expert guide, the tour takes you to five to six carefully chosen eateries, offering diverse tastings of Maine-inspired cuisine. 

Benefit from local insights into Portland’s dynamic food scene, all within an intimate setting for a more personalized experience. Perfect for those seeking traditional Maine delights, this tour unveils the flavors that define Portland’s gastronomic reputation.

Best for: food enthusiasts eager to explore the diverse and dynamic culinary scene of historic Old Port. Location: 94 Commercial St, Portland, ME 04101, USA

16. OTTO Pizza

Since 2009, OTTO Pizza has transformed the ordinary into the extraordinary. From their downtown Portland slice shop, Anthony and Mike have redefined pizza, experimenting with high-quality, local ingredients and creative toppings. 

From the unconventional “Masher” with mashed potato, scallion, and bacon to Thanksgiving dinner-inspired pies, every slice is a testament to their commitment to perfection and elevating the pizza experience. 

The OTTO story, born from two chefs with diverse backgrounds, showcases their passion for crafting serious and unforgettable pizza that transcends tradition, making it a culinary staple in Portland, Maine.

Best for: those seeking an extraordinary pizza experience. Location: 225 Congress St, Portland, ME 04101

17. Portland’s World of Flavors Tour

Begin a gastronomic expedition with Portland’s World of Flavors Tour , unveiling the diverse tastes that contribute to Portland’s culinary prowess. 

This 2.5-3 hour exploration through historic Old Port and waterfront areas showcases global influences, offering a cosmopolitan culinary journey. 

Experience flavors from Japan, Turkey, Mexico, and India, savoring locally sourced foods with international recipes, customs, and spices. 

Delight in an educational and entertaining experience, unraveling the cultural narratives behind each culinary gem. Designed for adventurous palates, this tour promises an exciting and memorable exploration of Portland’s rich culinary tapestry, making it a must for food enthusiasts visiting the city.

Best for: those who want to discover diverse global tastes that contribute to the city’s culinary prowess. Location: 230 Commercial St, Portland, ME 04101, USA

18. The Honey Paw

Awaken your taste buds at The Honey Paw, where the inspiration of a bear indulging in sweet honeycomb translates into a delightful dining experience. 

With steaming broths, savory wontons, and wok-fried noodles, The Honey Paw aims to hit that sweet spot you’ve been craving.

Best for: those who appreciate inventive and flavorful Asian-inspired cuisine. Location: 78 Middle St, Portland, ME 04101

19. Hot Suppa

Discover a delightful culinary journey at Hot Suppa with a diverse breakfast menu catering to all tastes. From the classic Buttermilk Waffle and Grandy Oats Organic Granola to unique specialties like Chicken and Waffle or Shrimp and Andouille Quiche, travelers can expect a satisfying and flavorful experience with each dish. 

The restaurant’s cozy atmosphere and extensive breakfast options make it a perfect stop for visitors seeking a hearty morning meal in Portland.

Best for: travelers seeking robust breakfasts. Location: 703 Congress St, Portland, ME 04102

20. Gross Confection Bar

Gross Confection Bar, a unique establishment in Portland’s Old Port District, is the creative vision of chef Brant Dadaleares. With a diverse culinary background working with renowned chefs, Brant creates component-based desserts and daytime bakery delights. 

The charming setting, housed in an 1883 building , offers a delightful experience where guests can explore the intriguing flavors and textures of Gross’s innovative creations. From breakfast sandwiches to brioche custard buns, the menu is a testament to Brant’s culinary artistry, making Gross a must-visit destination if you’re seeking exceptional desserts in Portland.

Best for: anyone looking for a yummy treat. Location: 172 Middle St, Portland, ME 04101

Portland, Maine is known for its vibrant and diverse craft brewery scene. The city has gained recognition for its numerous breweries, pubs, bars, and speakeasies, all of which offer a wide range of craft beers and unique brews. 

Here are some of the best places to quench your thirst in Portland.

21. Allagash Brewing Company

Allagash stands as a cornerstone of Portland’s vibrant craft beer scene. This place is so influential that its industrial park has become a hub for brewery startups. 

Rob Tod’s Belgian wheat beer, the White, catapulted Allagash to fame, earning it a reputation as a go-to light beer for IPA enthusiasts nationwide. While renowned for the White, Allagash excels in diverse beer offerings, ensuring there’s something to delight every beer aficionado. 

This brewery’s impact extends beyond its signature brew, shaping Portland’s beer landscape and contributing to the success of numerous breweries that emerged from its innovative surroundings.

Its delicious beer has even reached as far as NYC, which is where Mikey and I first discovered it long before we ever visited Portland.

Best for: craft beer enthusiasts, especially those who appreciate diverse and innovative beer offerings. Location: 100 Industrial Way, Portland, ME 04103

22. Lincoln Speakeasy

Lincoln Speakeasy, concealed below Market Street Eats, provides unbeatable drink deals at a flat $5 rate (hence the name, since it’s Abe Lincoln on the $5 bill). Though cash-only, the warm and friendly atmosphere invites patrons to unwind with budget-friendly cocktails. 

Everyone loves a good speakeasy and navigating the discreet entrance adds to the charm. Only those who are in the know can get in, so it’s a good thing I’ve provided the address below. 😉

Best for: those seeking budget-friendly yet charming cocktails in a discreet and exclusive setting. Location: Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

23. Eighteen Twenty Wines

Indulge in the unique experience of a rhubarb wine from Eighteen Twenty Wines. Thriving in Maine’s challenging climate, rhubarb, a hardy crop, becomes the star of Eighteen Twenty Wines.

Best for: Wine enthusiasts seeking a unique tasting experience. Location: Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

24. Hardshore Distilling Company

Experience the flavors of gin at Hardshore Distilling Company. Here, they enhance the spirits with diverse botanicals, transforming each liquor’s profile into a more complex and enjoyable taste.

Best for: those who appreciate the nuanced flavors of gin and enjoy exploring the intricate world of botanical-infused spirits. Location: Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

25. Maine Mead Works

A few years ago, my husband got really into D&D. Shortly after that, he got really into meads (is there a connection? Yes. Definitely). Well, his getting into meads got me into meads and now the rest is history. 

At Maine Mead Works, you can indulge in honey mead created in various flavors. If you visit, I recommend trying the Lavender Mead.

Best for: Dungeons & Dragons enthusiasts and mead lovers who appreciate exploring diverse honey mead flavors. Location: Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

26. Root Wild, a Kombuchery

Experience an array of kombucha flavors at Root Wild, a kombuchery (as termed by owner Reid). I’m not the biggest fan of kombucha (I’ve tried so hard), but I know lots of people who are and if that includes you, then Root Wild is a must-stop while in Portland. The open and stylish space, featuring details like kombucha-stained wood on the bar, added to the overall appeal.

Best for: kombucha enthusiasts and those who appreciate stylish, open spaces. Location: Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

27. Blyth & Burrows

Nestled on Exchange Street, Blyth & Burrows is a charming cocktail bar spanning two levels in an old brick building. Renowned for signature cocktails and a “small plates” menu, it also conceals a speakeasy in the back. 

Accessible through a secret staircase behind a bookcase, the speakeasy exudes an intimate, vintage ambiance akin to historic hideaways. Named in honor of naval heroes, Commander Blythe and Lieutenant Burrows, the establishment pays tribute to their sacrifice in a mural at the rear, commemorating a naval battle off the coast of Maine during the War of 1812.

Best for: cocktail enthusiasts seeking a charming, multi-level bar experience and speakeasy vibes. Location: 26 Exchange St, Portland, ME 04101

28. Pie North

Named after its unique location atop a pizza restaurant, Pie North is a speakeasy with an 80s arcade theme, brimming with nostalgia. Featuring retro-inspired musical decor and classic arcade games, it offers a distinctive and entertaining ambiance, making it a truly one-of-a-kind experience in Portland.

Best for: those seeking a unique and nostalgic experience, combining speakeasy vibes with 80s arcade fun. Location: 30 Market St, Portland, ME 04101

29. Austin Street Brewery

Founded in 2013 by friends Jake Austin and Will Fisher, Austin Street Brewery emerged from their shared passion for craft beer. After years of homebrewing in Westbrook, they self-financed their venture and opened on Industrial Way in Portland in 2014. Maintaining 100% ownership, they prioritize creative freedom and product excellence, utilizing 160 barrels across two facilities.

Best for: craft beer enthusiasts who appreciate independently owned establishments prioritizing creativity and product excellence. Location: 1 Industrial Way UNIT 8, Portland, ME 04103

30. Banded Brewing Co.

Established in 2013 by Ian McConnell, Banded Brewing, originally Banded Horn Brewing, proudly represents Biddeford, Maine’s inaugural brewery. 

The name symbolizes unity, reflecting the brewery’s commitment to collaboration and community. With a focus on balance, Banded Brewing crafts a diverse range of beers, blending traditional and avant-garde styles with a dedication to high quality.

Best for: those seeking a brewery rooted in community collaboration and beer diversity. Location: Building 13-W, 32 Main St, Biddeford, ME 04005

31. Battery Steele Brewing

Battery Steele Brewery originated in a South Portland barn in 2015, with the Flume Double IPA marking its initial pursuit of brewing perfection. Since then, the brewery has garnered loyal customers at its original tap room on Industrial Way in Portland and its kitchen and bar in Wells. 

Meticulously selecting high-quality ingredients, the brewery crafts innovative and world-class craft beers. 

The Wells location, Battery Steele Kitchen+Bar, near the beach, serves elevated pub food paired with exceptional beers. Committed to excellence, Battery Steele collaborates with local farmers and artisans, creating inviting atmospheres for remarkable beer and food experiences.

Best for: beer enthusiasts craving excellence, offering innovative craft beers at two vibrant locations. Location: 1 Industrial Way Units 12 & 14, Portland, ME 04103

As one of the most beautiful places in the country, Portland, Maine has a vibrant outdoor scene. From scenic trails and waterfront activities to picturesque parks, immerse yourself in the diverse outdoor offerings that make this coastal city an ideal destination for nature enthusiasts.

32. Walk or Bike Peaks Island

Peaks Island is a 720-acre haven for outdoor enthusiasts. And it’s all accessible by walking or biking—that is after you get off the boat and onto its sandy shores.

Peaks Island embodies a lifestyle defined by tranquility rather than any specific attraction. The island is home to around 1,000 year-round residents (swelling to 3,000 in summer), and prioritizes preserving natural beauty and a relaxed atmosphere. 

A mere 15-minute ferry ride from Portland makes it super convenient for anyone wanting to visit for a couple of hours or for a day trip. 

Best for: nature lovers who enjoy exploring tranquil charm. Location: Peaks Island

33. Set Sail With Portland Schooner Co.

Set sail on a unique and relaxing voyage through Portland aboard one of the three schooners, all of which are listed on the National Register of Historic Places. 

A sail with Portland Schooner Co. offers a laid-back experience, allowing you to appreciate the beauty of Casco Bay with the invigorating scent of sea air. It’s a perfect exploration mode for those who enjoy maritime charm.

Best for: sailing enthusiasts and those seeking a laid-back maritime experience. Location: 56 Commercial Street, Maine State Pier, Portland, ME 04101

34. Explore Munjoy Hill

Munjoy Hill is a neighborhood in Portland that seeps a lively blend of historical roots and modern charm. Situated on the elevated east end of Portland, it offers a fascinating journey through time. 

Originally settled way back in the 1630s and known for its working-class immigrant community, the area transformed in the 1990s with an infusion of artists and a thriving restaurant scene. 

The influx of artists brought about a dynamic mix of historic charm, trendy boutiques, and acclaimed eateries like Terlingua, all against the backdrop of the city’s finest view at the Portland Observatory (we’ll talk about that more in a bit).

Best for: history enthusiasts, art lovers, and those seeking a vibrant blend of historical charm and modern appeal. Location: Munjoy Hill

35. Scenic Walk Across the Eastern Promenade

Set on the edge of the ocean, Portland is home to a beautiful waterfront. Walking the 68.2-acre historic public park at the Eastern Promenade is just one of the ways to take in the serene sights. 

From its walking and running trails — both wooded and paved — to dog-friendly areas, boat launches, lively tennis matches, and serene beach days, this well-maintained and easily accessible park offers a splendid playground for a diverse range of visitors, providing a quintessential experience of what makes Portland a truly exceptional city.

This is another fantastic free activity in Portland!

Best for: nature enthusiasts, dog lovers, runners, beachgoers, and individuals seeking a serene and diverse outdoor experience. Location: East End

36. Lucky Catch Cruises

This immersive 90-minute maritime tour is not for the faint of heart but it promises a hands-on and educational exploration into one of New England’s vital industries: lobstering. 

Led by a close-knit team of experienced lobstermen, this excursion provides an authentic glimpse into the daily life of lobster harvesting. These seasoned professionals, who operate the tours between their fishing ventures, offer a genuine and up-close experience of where one of the nation’s most treasured foods originates.

Personally, as a vegetarian, I skipped this tour. But for those wanting to know more about where your food comes from, it’s highly rated with many claiming it’s a worthy experience in Portland.

Best for: those curious about the intricacies of lobstering, seafood enthusiasts, and individuals eager to explore the workings of a vital New England industry. Location: 170 Commercial St, Portland, ME 04101

37. Chill at East End Beach

While Maine’s Atlantic beaches are renowned for their cool waters locals swear by the invigorating experience of a dip on a hot day. East End Beach is the sole public beach in Portland (though there are others close by). So, if you’re visiting in the summer, be sure to bring your swimsuit!

➡️ For more tips on what to pack for Portland, Maine in the summer, check out my packing guide here !

This coastal haven draws crowds in the summer for sunbathing, water sports, and serene walks, making it an appealing year-round destination.

Best for: beach lovers, sun-seekers, and those looking for a refreshingly freezing dip on a hot day. Location: East End

38. Casco Bay Islands

While the town of Portland boasts only one public beach a wealth of shorelines awaits on the Casco Bay Islands nearby. 

Comprising six islands that are accessible year-round, each island in Casco Bay has its distinct personality, history, and array of attractions and activities. 

Among them, Cliff Island stands out as the smallest, home to just 60 full-time residents, featuring unpaved roads and a serene, secluded ambiance, making it a tranquil outdoor retreat with limited attractions to draw in crowds.

Best for: travelers seeking diverse coastal experiences and tranquil retreats. Location: Casco Bay

39. Catch a game at Hadlock Field

If you’re a baseball fan, you’re going to want to catch a swing at Hadlock Field. This is where the Sea Dogs play, a local minor league baseball team that dominates in the summer.

Best for: baseball buffs and sports fans. Location: 271 Park Ave, Portland, ME 04102

40. Palace Playland

Calling all adrenaline junkies, Palace Playland is one of the best things to do in Portland, Maine!

Okay, so it’s not exactly in Portland. But it’s close enough and worth the drive. Located approximately 20 miles south of Portland in Old Orchard Beach, this 5-acre amusement park stands as New England’s sole beachfront amusement destination.

The park boasts a 24,000-square-foot arcade, offering over 200 classic games like Skee Ball and air hockey. In addition to the extensive game selection, the park offers exhilarating rides like the Sea Viper roller coaster. The amusement park also features a variety of rides suitable for younger visitors, including a carousel and spinning tea cups.

Best for: families and thrill seekers. Location: 1 Old Orchard St, Old Orchard Beach, ME 04064

41. Back Cove Trail

Stroll along the 4.2-mile Back Cove Trail loop. In addition to enjoying the peaceful scenery, you can also do a bit of active manifesting by visualizing you own one of the spacious waterfront residences you’re walking by.

Best for: those who appreciate scenic walks and harbor aspirations of waterfront living. Location: 43.6723309°N 70.268200°W

42. Stand-Up Paddle Sunset Tour in Portland

Experience the serene beauty of Casco Bay at sunset with the Stand-Up Paddle Sunset Tour in Portland . 

This two-hour excursion is suitable for all skill levels and offers a leisurely paddle along the Eastern Promenade Trail. The tour provides panoramic views of the sun setting over the city as you glide past the undeveloped coastline and seals on the ledges near Mackworth Island. 

Included are a stand-up paddleboard, paddle, and lifejacket, along with a dry bag for your belongings.

Best for: nature lovers and those seeking a peaceful sunset experience on the water, regardless of paddleboarding skill level.  Location: 1 Cutter St, Portland, ME 04101, USA

43. Sea Kayak to an Island Tour in Casco Bay

Venture on a captivating three-hour Sea Kayak Tour in Casco Bay , starting from Mere Point in Brunswick. Led by a professional guide, you’ll paddle through NW Casco Bay, visiting different islands, and savoring the chance to spot marine birds and seals. 

You can choose a single or two-person kayak and snacks and safety gear are provided. (Always love when a tour provides snacks!)

With group sizes capped at eight participants, you can feel safe on this tour as you receive individual attention from your guide. 

The adventure includes a stop on an island for homemade hot muffins, tea, lemonade, and exploration before returning to the starting point.

Best for: nature lovers, kayaking fanatics, and those looking for a guided exploration of Casco Bay’s islands, wildlife, and coastal beauty. Location: 1161 Mere Point Rd, Brunswick, ME 04011, USA

Portland has a rich cultural tapestry that you can explore through its diverse museums. Each gallery offers a unique glimpse into the city’s history, art, and maritime heritage. 

From immersive exhibits to captivating artifacts, explore the vibrant museum scene that reflects the essence of this endearing coastal city.

44. Victoria Mansion

Enthusiasts of architecture and interior design will be captivated by the splendor of the Victoria Mansion, also known as the Morse-Libby House or Morse-Libby Mansion. 

Originally constructed in the mid-1800s as a summer residence for hotelier Ruggles Sylvester Morse, this National Historic Landmark showcases pre-Civil War grandeur. With its exterior modeled after an Italian villa and intricate features such as a square tower, balconies, and piazzas, the mansion is a testament to historical opulence. 

Inside, preserved by the work of renowned designer Gustave Herter, the museum boasts 90% of its original interiors, featuring carved wood panels, gas light fixtures, and ornate decor.

Best for: admirers of historical architecture and interior design aficionados. Location: 109 Danforth St, Portland, ME 04101

45. Wadsworth-Longfellow House

Constructed post-Revolutionary War, the Wadsworth-Longfellow House served as the residence for four generations of a distinguished family, commemorated today in this museum for their significant contributions to American culture. 

Notably, 19th-century poet Henry Wadsworth Longfellow, a prominent figure in the family, spent his formative years in this historic home. 

Beyond its association with the revered poet, the household has broader historical importance as the oldest standing structure on the Portland peninsula , the inaugural brick dwelling in the region, and Maine’s pioneer home museum.

Best for: history enthusiasts and literary admirers. Location: 489 Congress St, Portland, ME 04101

46. Portland Museum of Art

Portland might not be the biggest city in the States, but it’s got one heck of an art scene. The Portland Museum of Art houses works by renowned figures such as Andy Warhol, Claude Monet, and Winslow Homer. 

The Portland Museum of Art features an extensive collection of American, European, and contemporary art, as well as pieces by Maine artists. 

With over 18,000 items in its collection, including paintings, photographs, sketches, pottery, furniture, silverware, sculptures, and more, you’re going to find something new every time you visit. 

The museum also hosts regular events, including movie screenings, curator talks, and family-focused activities, so make sure to check ahead to see if there’s anything fun scheduled during your trip.

Speaking of which, if you’re super into art, you might want to consider planning your visit to coincide with a First Friday Art Walk. On the first Friday evening of each month, the Arts District buzzes with art enthusiasts exploring local galleries and venues on self-guided tours. Street performers, musicians, and artists of various disciplines showcase their talents in the streets.

Best for: art enthusiasts, culture aficionados, and those who appreciate a vibrant art scene. Location: 7 Congress Square, Portland, ME 04101

47. Children’s Museum and Theatre of Maine

For family-friendly fun in Portland, don’t miss the Children’s Museum and Theatre of Maine. With over 30,000 square feet of space, this museum is one of the best things to do in Portland, offering interactive learning experiences and enjoyment for visitors of all ages.

Best for: families seeking interactive learning experiences and enjoyable activities for visitors of all ages. Location: 250 Thompsons Point Rd, Portland, ME 04102

48. Tate House Museum

Built in 1755 for Captain George Tate, the Tate House served as the residence for this British Royal Navy senior mast agent and his family. 

Responsible for transporting white pines, Maine’s state tree, to England, Tate’s role is explored through hourly site tours showcasing artifacts, furnishings, and the grounds. These elements not only illuminate the 18th-century lifestyle of the Tate family but also emphasize the significance of the mast trade during the era. 

Located approximately 4 miles west of downtown Portland, the Tate House stands as the only pre-Revolutionary home open to the public, offering visitors an educational glimpse into history.

Best for: history enthusiasts and those intrigued by 18th-century life. Location: 1267 Westbrook St, Portland, ME 04102

49. Maine Narrow Gauge Railroad Co. And Museum

Located approximately 1.5 miles from the Portland Museum of Art, the Maine Narrow Gauge Railroad Co. and Museum provides insights into train preservation and Maine’s narrow gauge railway history. 

This distinctive two-foot gauge railway system, featuring tracks less than half the width of standard gauges, was a cost-effective solution for traversing Maine’s challenging landscapes of forests, rocky hills, and mountains, connecting rural areas with larger cities from the 1870s to the 1940s.

Best for: railway aficionados and those curious about Maine’s transportation history. Location: 49 Thames St, Portland, ME 04101

50. International Cryptozoology Museum

Everybody knows a bigfoot enthusiast. And if no one comes to mind, then odds are you’re probably the cryptid lover in your family. Either way, the International Cryptozoology Museum is a fun way to spend your day in Portland.

Explore the realm of hidden creatures like Bigfoot and Nessie through the study of Cryptozoology, and immerse yourself in the intriguing exhibits at the International Cryptozoology Museum in Portland.

Best for: fans of the creepy, unusual, and cryptic. Location: 32 Resurgam Pl, Portland, ME 04102

51. Portland Fire Museum

Portland has been totally destroyed by fire a total of four times since its inception. Discover the history of fires in the area by exploring the exhibits at the Portland Fire Museum.

Best for: history enthusiasts, especially those fascinated by the impact of fires on urban landscapes. Location: 157 Spring St, Portland, ME 04101

52. Umbrella Cover Museum

Want to visit a museum unlike anything you’ll find in another city? Visit the Umbrella Cover Museum, a gallery that exclusively celebrates umbrella covers.

Best for: quirky museum enthusiasts and those with a taste for the unconventional. Location: 62 Island Ave, Portland, ME 04108

Explore Portland’s vibrant arts and culture scene, where the city’s historic and contemporary influences converge. Immerse yourself in world-class museums, eclectic galleries, and dynamic performances, all showcasing the creativity of Portland’s artistic identity.

53. Catch a show at Thompson’s Point

Nestled on the Fore River, Thompson’s Point merges nature and culture with its open-air venue set amid three acres of picturesque lawns. Collaborating with the State Theatre of Portland, the space hosts acclaimed concerts and year-round festivals. 

Summers feature artisanal markets, while winter transforms the site into a family-friendly skating rink. Throughout the seasons, epicurean delights from renowned food trucks add to the allure of this dynamic destination.

Best for: culture enthusiasts and music lovers. Location: Thompson’s Point

54. Explore The Arts District & First Friday Art Walk

The Arts District in Portland offers a rich melting pot of creativity, encompassing diverse expressions from stage performances to museum sculptures. Embracing independent thinking, the district showcases the city’s cultural mindset. 

Don’t miss the First Friday Art Walk, a monthly self-guided tour, for an immersive experience in the vibrant arts scene.

Best for: those who appreciate diverse expressions, from stage performances to museum sculptures. Location: Upper Congress Street toward the city’s West End

55. Portland Observatory

The Portland Observatory is a historic maritime signal tower dating back to 1807. This famed observatory offers unparalleled harbor views that you won’t find anywhere else in the city.

Here, Captain Lemuel Moody, the observatory’s founder, provided ship alerts for a fee, and with a telescope, he could spot vessels from 30 miles away. Though replaced by radio, the observatory’s charm and history remain, making it a must-visit.

Best for: history enthusiasts and those seeking breathtaking harbor views. Location: 138 Congress St, Portland, ME 04101

56. Portland Farmers’ Market

Maine has had a longstanding commitment to local agriculture and Portland’s vibrant farmers’ market is a testament to that commitment. Here, over 40 growers, cheesemakers, beekeepers, bakers, and more gather twice a week in summer and fall, and weekly in winter.

Best for: farm-to-table devotees and supporters of local agriculture. Location: Deering Oaks Park on Saturdays, Monument Square on Wednesdays; Stevens Avenue on Saturdays.

57. Coastal Maine Botanical Gardens

Coastal Maine Botanical Gardens is a New England gem that was born from a 16-year dream. The park spans over 300 acres and features themed gardens showcasing the diverse flora of Maine, including dahlias, bees, and rhododendrons. 

While the botanical gardens are not technically located in the city center, it’s not too far of a drive located 60 miles northeast of Portland. This park is worth the visit and stands as the largest botanical garden in the region.

If you’re visiting Portland during the holidays, experience extra magic at the Coastal Maine Botanical Gardens with the dazzling light displays of Gardens Aglow, illuminating the winter darkness on select nights. 

Best for: nature enthusiasts, garden lovers, and those seeking a serene escape. Location: 105 Botanical Gdns Dr, Boothbay, ME 04537

58. Walk through the East Cemetery

Tap into your inner witch and wander through the more historic side of Munjoy Hill by strolling through the East Cemetery, Monjoy’s oldest historical site. If you’re feeling especially gothic, stop by the Dead House, a structure once used to store bodies during winter until the spring thaw. 

This is the perfect free activity in Portland for people who love to add a little bit of macabre into their travels!

Best for: history enthusiasts and those with a taste for the gothic. Location: 224 Congress St, Portland, ME 04101

Uncover Portland’s rich history and vibrant culture with guided tours offering insights into its culinary delights, historic neighborhoods, and iconic landmarks. I always love a good tour because you can engage in expert-led explorations and gain a deeper understanding of a city’s unique stories and hidden gems.

59. Vintage Fire Truck Sightseeing Tour of Portland, Maine

In this one-of-a-kind tour, you’ll enjoy panoramic views from a red fire engine as you discover picturesque lighthouses, historic landmarks, and vibrant neighborhoods. 

On the Vintage Fire Truck Sightseeing Tour of Portland, Maine , you’ll delight in live narration from your guide, unraveling the maritime past and exploring cobblestone streets. Immerse yourself in the Old Port’s charm, with its boutiques, pubs, and lively dining scene. 

This fun and informative tour offers a great overview of the city’s highlights, providing an unforgettable experience for visitors eager to see Portland’s beauty and history in a distinctive way.

Best for: those seeking a unique and panoramic experience of Portland. Location: 180 Commercial St, Portland, ME 04101, USA

➡️ Plan A Day Trip To Portland, Maine Using This Done-For-You Portland Maine Day Trip Itinerary .

Where to Stay in Portland, Maine in 2024

Portland’s hotel prices can be on the higher side, with a survey by Cheaphotels.com 1 ranking it as the second most expensive city for hotels in the United States. 

While I was visiting Portland with my family, we went on a tour of the Customs House and were jokingly informed that the hotels in the area were so pricey that one could potentially charge $250 a night to rent out the 12-square-foot bank safe hidden in the building.

Given the expense of Portland hotels, a great alternative is to consider staying in an Airbnb or VRBO .

Nestled in the charming town of Scarborough, we found a delightful Airbnb hosted by Steven. The Rustic Suite near downtown Portland and Beaches lived up to its listing, offering a cozy, clean, and comfortable retreat.

The space is a studio apartment with a master bed in the front, an additional room in the back creating a family room/TV space, and a super fun loft area with two twin beds overlooking the family room. This unique setup provided more comfort than a traditional hotel and allowed us to explore the historic neighborhood surrounding one of the U.S.’s oldest towns.

Conveniently located just a 10-minute drive from downtown, this pet-friendly accommodation was a perfect choice.

If vacation rentals aren’t your preference or you wish to stay closer to downtown, here are some highly recommended hotels in Portland, Maine:

📍 Luxury: The Press Hotel

For a blend of history and luxury, indulge in a stay at the Press Hotel . 

Occupying a century-old building that was once home to the Portland Press Herald newspaper, this pet-friendly 4-star hotel in the heart of downtown offers refined details, distinctive features, and a rotating art gallery. 

While it may be on the pricier side, a night at the Press Hotel ensures an unforgettable experience in Portland.

📍 Mid-range: The West End Inn

Opt for the charming West End Inn for a mid-range lodging experience. Situated in downtown Portland, this inn provides convenient access to key attractions, including the Victorian Mansion, just a half-mile away. Enhance your stay with a delightful breakfast menu and themed dinner nights.

📍 Budget: Holiday Inn Portland-by the Bay

For a more budget-friendly option without sacrificing impressive views and valuable amenities like parking and e-bikes, consider the Holiday Inn Portland-by the Bay . Who needs luxury living when you have an entire city to explore?

📍 Hostel: Black Elephant Hostel

If you’re seeking budget accommodations with a touch of vibrancy, the Black Elephant Hostel is your ideal choice. 

This colorful and fun hostel, the first and only one in Portland, was created with the mission of uniting people and cultures, bringing hostel culture to this historic New England town.

➡️ For a complete guide on where to stay in Portland, check out my blog reviewing the 15 Best Unique & Historic Hotels in Portland, Maine here.

Getting around Portland, Maine

Navigating the downtown area of Portland is a delightful stroll, and once you’ve parked your car, you might find you won’t need it until you’re ready to bid adieu to the Old Port area.

However, if your adventures lead you to explore lighthouses or other attractions beyond the city center, you’ll want reliable wheels. Here are transportation options to consider during your stay in Portland.

While the city center offers a charming walkable experience, reaching attractions like lighthouses may call for alternative transportation. 

Portland provides an adventure-filled option with numerous well-marked bike lanes in and around the city. Many hotels offer bike rentals for day use, and public bikes are available, allowing you to pedal your way around and explore the sights. 

Keep in mind that biking is a leisurely mode of transportation, so plan your itinerary accordingly to ensure ample time at each destination.

For a convenient city-wide experience, Portland boasts a reliable bus service, known as METRO. The easiest way to pay for rides is with cash. It’s advisable to have some loose change on hand, as each journey typically ranges from $1 to $4 and you’ll need exact change. 

Some locals have been navigating Portland without a car for years, relying solely on the efficient bus system.

Opting for popular ride-sharing services like Uber or Lyft is a pricier yet quicker and more convenient alternative, especially when time is of the essence during your day in town. This option is less expensive than renting a car. It’s also a responsible decision if you plan on indulging in local brews and need a safe ride back to your accommodation.

For the utmost flexibility, exploring Portland by car is the easiest way to get around. Navigating the city is straightforward, and though parking may be a bit pricey, there are plenty of options, including paid lots, on-street parking, and garages. 

Metered parking is a cost-effective choice at $2.50 per hour. Keep in mind that on-street parking in Portland is complimentary from 6 p.m. until 9 a.m., Monday through Saturday, as well as all day on Sundays and major holidays. To streamline your parking experience, consider using the PassportParking App .

Whether you’re pedaling, hopping on a bus, summoning a ride-share, or navigating the city on four wheels, Portland ensures you have convenient options to make the most of your visit.

What to Pack for Your Trip to Portland, Maine in 2024

When exploring the coastal regions of Maine, like Portland, be prepared for cooler temperatures, even in summer. Ensure you pack suitable cold-weather attire such as pants, sweaters, long shirts, and waterproof shoes.

Use this packing list to make sure you remember to bring everything you need on your trip to Portland, Maine.

Clothing and footwear

You may already have an idea of what to pack for Portland, Maine. But make sure you also include these three essentials.

Hiking Boots

Choose waterproof, durable hiking boots for comfort whether trekking mountains or strolling through the city.

View on Amazon.com →

Breathable Water Shoes

Opt for water shoes in Portland’s rainy hikes or if you decide to take a dip at a nearby beach. These breathable water shoes protect your feet, offer traction, and are easy to clean.

Stylish Dress

Portland is a down-to-earth city, but you still might want to dress up for a night out on the town. Whether you’re going out to dinner or enjoying time at a brewery, this comfortable, bohemian floral print split dress will have you feeling glammed up and fantastic for your Portland vacay pics.

While you probably know your basic toiletries by heart, don’t get on that plane to Portland without double checking you have these items.

Solid Shampoo Bar

Instead of your regular liquid shampoo, opt for a spill-proof, eco-friendly shampoo bar like Love Beauty and Planet’s 2-in-1 vegan option . It’s much more convenient for traveling.

Insect Repellent

If you’re visiting Portland in the summer and plan on doing outdoor activities, you’re going to need some bug spray . Opt for this quick-dry, weather-resistant, organic spray for comfort and protection against bugs.

Hand Sanitizer

Portable hand sanitizer is a travel essential, offering cleanliness on the go, especially during outdoor adventures.

Toiletry Bag

And to tie it all together, you’ll need something to keep all your necessities together. This TSA-approved toiletry bag is the perfect container to keep your essentials organized.

Travel Essentials

These travel essentials are going to make your trip to Portland so much easier.

Portable Windproof Umbrella

Stay dry in Portland’s rain with a portable windproof umbrella , ensuring a comfortable and enjoyable exploration.

Travel Packing Organizers

Maximize packing efficiency with these packing cubes —compact, organized, and ideal for Portland’s bulky fall and winter items.

Compact Portable Charger

Keep your phone charged on the go with this small portable charger that slips in the pocket of your pants or bag. Snap as many pics as your heart desires knowing you can charge your phone, even on the go.

Travel Insurance

Ensure peace of mind on every trip with World Nomads Travel Insurance , offering affordable and comprehensive plans for all.

Evaluate insurance plans on World Nomads Travel Insurance →

➡️ For a more detailed Portland packing list, check out my complete Portland packing guide for any season here .

FAQs About Visiting Portland, Maine

You’re almost ready to set sail to one of the United States’ most charming coastal towns. Before you start your trek, let’s go over some frequently asked questions about visiting Portland, Maine.

Portland, Maine is absolutely worth visiting! Portland is a picturesque coastal city with a rich history, vibrant culture, and diverse attractions, making it well worth a visit.

Yes, Portland is compact and offers a lot to explore, making it perfect for a rewarding day trip filled with unique experiences.

While a day trip can cover key attractions, spending 2-3 days allows for a more leisurely exploration, enjoying the city’s diverse offerings.

The best time to visit is during the summer and early fall when the weather is pleasant, and outdoor activities are abundant. Fall foliage adds extra charm.

While Acadia National Park is approximately 3 hours away, a day trip is possible but may be rushed. Consider an overnight stay for a more relaxed visit.

Explore indoor attractions like museums, art galleries, and cozy cafes. Attend a live performance or indulge in the city’s vibrant culinary scene.

Options include renting a car, taking public transportation, or joining guided tours. Consider day trips to coastal towns, lighthouses, and nature reserves.

Want to explore more in Maine? Check out this Central Coastal Maine Private Day Tour . 

This 6 to 8-hour tour will show you around Portland first and then take you and your group on a wild adventure across the coast of Maine. You’ll visit historical sights, picturesque locations, and charming coastal villages.

So there you have it, folks! From exploring historic neighborhoods to savoring local cuisine, there are so many more things to do in Portland, Maine than people realize. 

As you plan your visit to Portland, I hope this guide sparks excitement and anticipation for the adventures that await. If you’re eager to make the most of your trip, don’t forget to check out my detailed guide, Perfect Day Trip to Portland, Maine: The Best 1-Day Itinerary . It’s packed with insights, recommendations, and hidden gems to elevate your experience. 

So pack your bags and embrace the small-town feel of the coastal city. With so much to do, you’ll likely find yourself visiting Portland over and over again. 

Was this guide useful? Check out our other Portland content here:

• Perfect Day Trip to Portland, Maine: The Best 1-Day Itinerary
• The Complete 2024 Portland, Maine Packing List For Any Time Of Year
• A Walk Through Time Tour in Portland — Genuine Travel Review

The 5 Most Beautiful Lighthouses in Portland, Maine

• Where to Stay in Portland, Maine: The Ultimate Guide in 2024
• Ultimate Guide to Walking Tours in Portland, Maine in 2024

Additional Resources:

Ready to book your portland, maine, trip.

Here are a few helpful services:

Booking.com | Find a comfy place to lay your head after a full day of adventuring.

Vrbo | If you’re looking for a more homey vibe, these rental homes might do the trick.

Expedia | Whether you’re looking for some wheels or a flight, you can find a way to get to your destination here.

Get Your Guide | Find local attractions and tours and book tickets to your excursions.

Viator | Another great resource for local attractions and tours.

TSA | If you’re flying, check out the TSA page to make sure that you pack to TSA regulations.

World Nomads Travel Insurance | Feel safe while traveling with simple and flexible travel insurance.

Taking a quick day or weekend trip over to Portland? Check out my recommended itinerary for what to do in Portland for a day .

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18 Best Things to Do in Portland, According to a Maine Local

Delicious seafood restaurants, beautiful island excursions, and cool breweries await.

When it comes to finding things to do in Portland, Maine, there's no one itinerary that fits all. The Pine Tree State's largest city is filled with maritime history, waterfront trails, and a slew of artisanal shops, award-winning restaurants, and craft breweries.

As a lifelong Mainer and former Portland resident, I can recommend a few things to keep in mind when planning your trip. For starters, pack some comfortable shoes and layers (even the hottest of summer days come with brisk nights).

Portland is essentially divided into two parts: on-peninsula (where the bulk of the following recommendations are located) and off-peninsula (including the outskirts and many residential neighborhoods). Walking, biking, taxis, and public transportation are all options if you mainly plan to stay on the peninsula. If you want to explore the outskirts of town, you'll likely need a car. Parking can be complicated, especially during peak travel months, so you may want to choose a hotel that offers it (such as The Francis, where it's free for guests).

From historical trails to island excursions, here are 18 of the best things to do in Portland, Maine.

Walk along the Eastern Promenade.

For a quintessential waterfront stroll, set off along the Eastern Promenade Trail from downtown Portland. The two-mile path is one of several in the park of the same name , designed by the renowned Olmsted Brothers in the early 1900s. Along the way, look out for the many migratory birds that make a rest stop here, and grab a bite from the food trucks in the Cutter Street parking lot. The East End Beach (which is more rocks than sand) is a scenic spot to take in the views of Casco Bay or rent a kayak for a different perspective of the city. If you want to explore further, the promenade links to the Back Cove Trail and Bayside Trail .

Enjoy the view from the Portland Observatory.

Get a 360-degree panorama of the city from atop the 86-foot-tall Portland Observatory . You can climb the seven flights of stairs at your own pace or request a guided tour for a deeper dive into the legacy of the building. The tower, which dates from the early 1800s, is the only remaining historic maritime signal station in the United States. Open from late May to early October, it's run by the nonprofit Greater Portland Landmarks , which also offers walking tours of various Portland neighborhoods.

Have a drink at Luna Rooftop Bar.

The Canopy by Hilton has a prime location on the Portland waterfront, and its rooftop bar and restaurant, Luna , has become a favorite among hotel guests and locals since it opened in 2021. Small bites and artisanal cocktails await with a panoramic view of the harbor from the sixth-floor vantage point. If you happen to book a stay at the hotel, don't miss the pastries and specialty lattes at Salt Yard , located on the street level.

Visit the art gallery in The Press Hotel.

Housed in the former headquarters of the Portland Press Herald, The Press Hotel is one of the best luxury hotels in Maine . Even if you're not staying here, it's worth popping by the property's lower-level art gallery, which is open to the public and spotlights the state's emerging and established creatives. Stick around for a beverage in the lobby bar, which pays homage to the glory days of journalism with an installation of 62 vintage typewriters.

Check out an event at Thompson's Point.

Thompson's Point is a one-stop spot for entertainment, a children's museum, and year-round special events (it even has a skating rink in the winter). In the summer, the venue offers free live music at sunset and ticketed concerts in partnership with the State Theatre , as well as a wide selection of food trucks and places to grab a beer, wine, or coffee. On select Sundays, the restored railroad shed hosts the Maker's Market, where you can shop for pieces from local artisans while sipping mimosas from the bar.

Go brewery hopping.

With a craft beer scene like Portland, picking just one brewery to visit is impossible. The Maine Brews Cruise offers behind-the-scenes walking and bus tours of the city's pubs and breweries. Those wanting to experience Portland's breweries on their own time can check out the Maine Brewers' Guild's route planner , which allows you to build a personalized itinerary and map.

Eat tacos at Bird & Co.

While many visitors have their taste buds set on fresh Maine seafood (and rightly so), this taco joint should not be skipped. Thankfully, the 12 taco varieties are sold individually because the creative menu will likely have you ordering one of each (or close to it). Vegan and vegetarian options are deliciously celebrated, too.

Admire masterpieces at the Portland Museum of Art.

Whether you're a museum lover or simply looking for things to do in Portland on a rainy day, you can't go wrong with a visit to Maine's largest and oldest public art institution. Founded in 1882, the Portland Museum of Art features temporary exhibits and a permanent collection with over 19,000 works, including pieces by Andy Warhol and Claude Monet. The museum spans three architecturally stunning buildings in the city's vibrant Arts District and boasts a great sculpture garden. Check out the calendar to see what's on, or plan your visit around the free admission times, including Friday evenings and every third Thursday of the month.

Take the ferry to Peaks Island.

One of the best things to do in Portland (or anywhere in Maine, for that matter) is to get out on the water — especially in the summer. For a few dollars each way, a 20-minute ride to the islands of Casco Bay will let you bask in the ocean air, and the frequent ferry schedule makes it easy to fit into your itinerary. On the charming Peaks Island, you can find a quiet picnic spot, enjoy ice cream from Down Front or a cinnamon bun from Peaks Cafe, and stop by the one-a-kind Umbrella Cover Museum . Kayak and bicycle rentals are available (though golf carts are the preferred method of transportation). For a longer getaway from the city, spend the night at The Inn on Peaks Island.

Shop at The Black Box.

Located on the popular strip of Washington Avenue, The Black Box is a series of repurposed shipping containers that provide small businesses with a physical space to operate. Current retailers include Moonday Coffee, Thicket Jewelry, and Pinebury activewear. Since this is an incubator space, check the website for the most up-to-date businesses.

Ride the Maine Narrow Gauge Railroad.

This family-friendly railway takes passengers on 40-minute train rides along the Eastern Promenade with scenic views of Casco Bay. Save some time to roam the museum before or after the ride. In the summer, there's the Ice Cream Train, where every passenger gets a cone, and winter brings the festive Polar Express, based on the popular Christmas movie.

Discover hidden gems on Stevens Avenue.

There's a small stretch of Stevens Avenue in the Deering Center neighborhood that's not to be missed. Grab a coffee at Rwanda Bean , where 50 percent of the profits go back to the farmers. Then, check out The Honey Exchange to learn about beekeeping and peruse some home goods, natural beauty and health products, honey-based items, and local beverages. Darby Jones , a boutique that dubs its carefully selected wares as "desirable nonessentials," is a great alternative for typical souvenirs.

Chow down on fresh seafood at Luke's Lobster.

There's a certain buzz and sense of place that comes with dining within arm's reach of a working waterfront. Seeing the fisherpeople pull up with the day's catch connects diners at Luke's Lobster with their meal and the local community. But it isn't just the fresh seafood that's to be celebrated. Luke's Lobster has outposts around the globe, including an online market, and it's proud of its sustainable practices and Certified B Corp status.

Catch some live music.

Portland attracts an array of musicians and artists, and is home to multiple venues for performers. Portland House of Music , One Longfellow Square , State Theatre , Blue , and Merrill Auditorium are among the most popular spots to enjoy a concert.

Go lobstering with Lucky Catch Cruises.

Experience a day in the life of a lobster fisher with Lucky Catch Cruises , which offers interactive excursions focusing on Maine's most important food export. During the 90-minute tour around Casco Bay, you can try your hand at hauling up the traps and enjoy the scenic views of the coast, historic forts, and lighthouses. After the cruise, purchase some lobster at the wholesale price — the restaurant next door, Portland Lobster Company , will happily cook your catch for you.

Wander the cobblestone streets of the Old Port.

The Old Port is a section of downtown Portland that's home to 19th-century red brick buildings, cool boutiques, bars, restaurants, nightclubs, and live entertainment venues. Even when Portland's population soars from 66,000 to more than two million in the summertime, there's a quaint vibe to this part of the city. Pair your visit with a sail with Portland Schooner Co. , which offers two-hour Windjammer cruises around the bay.

Stop by Maine's oldest bookstore.

Founded in 1886, Sherman's Maine Coast Book Shop has several locations around the state, including one in the heart of Portland on Exchange Street. Here, you can find books by local authors, as well as those on the bestseller list. Sherman's also sells gifts, toys, and a variety of Maine-made specialty items.

Grab a bite at The Porthole.

Yes, it will be busy, but The Porthole is simply one of those places you have to experience in Portland. The hole-in-the-wall restaurant opened on the waterfront in 1929 to fuel fishermen early in the morning before they went out for a day of laborious work. May we suggest the lobster Benedict for breakfast and baked stuffed haddock for dinner?

Related Articles

Guide to the Old Port | Eat, Stay & Play in Portland, Maine

Cobblestone streets, salty ocean air, and boutiques and eateries aplenty characterize Portland’s historic Old Port district.

By Cathryn McCann

Jun 29 2022

Guide to Old Port | Harbor

Wandering the Old Port district in Portland, Maine, you may feel as though you’ve stepped onto a movie set. With its cobblestone streets, 19th-century brick buildings, fishing piers, and location overlooking the Fore River, the southeastern side of Portland has a historical feel (and is listed on the National Register of Historic Places), while its boutiques, restaurants, bars, and nightlife make it a popular destination for modern-day tourists. Here are some of our favorite things to do, places to stay, and places to eat in the Old Port.

Old Port in Portland, Maine | Things to Do

Portland schooner co..

Given Portland’s prime oceanside location, it’s hard for visitors to resist the urge to get out and explore on the water. Fortunately, you can hop aboard an early-1900s windjammer with the Portland Schooner Co. to enjoy some of Maine’s most beautiful sights.

While wandering the Old Port, be sure to stop in to some of the many boutiques lining the streets. Cool as a Moose on Fore Street is the place for fun Maine apparel and souvenirs, and you can find beautiful, locally made (and often handcrafted) goods at Lisa-Marie’s Made in Maine  on Exchange Street. Old Port Candy Co. on Fore Street will satisfy your sweet tooth with a dozen flavors of fudge and an array of chocolates ranging from peanut butter to sea salt and bacon.

Plan Your Perfect Summer Adventure: Get The Free Ultimate New England Summer Guide!

Harbor Fish Market

If sniffing the salty ocean air puts you in the mood for some seafood, your go-to destination in the Old Port is the Harbor Fish Market, Here, you’ll find a wealth of fresh seafood, ranging from lobster and haddock to rarer finds like dorado and soft-shell crab.

Lucky Catch Cruises

Experience what it’s like to be a Maine fisherman aboard one of the Lucky Catch Cruises . Take in the sights of Casco Bay while hauling up lobster traps from the bottom of the ocean and learning about one of Maine’s favorite crustaceans.

Old Port in Portland, Maine | Restaurants

Central Provisions

Located in a Federal-style brick building on the corner of Fore and Dana streets, this rustic-chic restaurant can likely deliver whatever you’re in the mood for. There’s a raw bar, cold and hot plates, sweets, bar snacks, cocktails and punches, plus a full brunch and lunch menu.

This small, bustling restaurant is famous for its hand-cut Maine potatoes fried Belgian-style in duck fat (hence the name), tossed in seasoning and served in a paper cone with five homemade dipping sauces. Among the other casual-dining treats here are poutine and milkshakes.

The Holy Donut

This cult-favorite shop serves up fresh, handmade Maine potato doughnuts in flavors such as maple, coffee brandy, sea salt, and toasted coconut. There’s a doughnut for everyone here — even gluten-free and vegan options!

Eventide Oyster Co.

Especially beloved for its brown-butter lobster roll , Eventide is an upscale, modern-day oyster bar that offers tasty seafood of every kind, a New England clam bake, and a menu that changes daily.

This trendy eatery puts a Mediterranean spin on classic Maine dishes. Floor-to-ceiling windows make it great for people-watching, and you can also see the chefs working their magic in the open kitchen.

The Honey Paw

For a superlative bowl of noodles — and much more — head to the Honey Paw on Middle Street. The house-made noodle dishes range from ramen and yaki soba to lobster curry, while the rest of the menu is filled with things such as fried chicken, sandwiches, and appetizers like wok-charred bok choy.

Old Port in Portland, Maine | Hotels

Black elephant hostel.

Portland’s first and only hostel features vibrant outdoor murals, funky decor (think geometric wallpaper and recycled wood furniture), a full shared kitchen, 13 bathrooms, and large hall sinks. The family-run establishment has women-only and men-only rooms, as well as co-ed rooms and several private rooms.

The Press Hotel

This award-winning boutique hotel is recognizable from afar, thanks to its iconic “Press” sign on the side of the historic building that once housed the Portland Press Herald . Each of the 110 guest rooms has newsroom references and all the modern amenities; elsewhere in the hotel you’ll find an on-site restaurant, an art gallery, and a fitness center.

Portland Harbor Hotel

The decor at this waterfront hotel — which offers 101 rooms and suites— has a charming coastal/nautical vibe, while amenities include complimentary bicycle use, free coffee, a fitness center, outdoor dining, and an outdoor fire pit. Plus, it accommodates pets for a small fee.

Have you ever been to the Old Port? Tell us about it!

This post was first published in 2018 and has been updated. 

SEE MORE: Portland, Maine | Restaurants & Eateries Guide Best Things to Do in Portland, Maine Portland, Maine | Hotels & Inns Guide

Cathryn McCann

As Digital Assistant Editor, Cathryn writes, manages, and promotes content for NewEngland.com and its social media channels. Prior to this role, she lived and worked on Martha’s Vineyard as a newspaper reporter, covering everything from environmental issues and education to crime and politics. Originally from New Hampshire, Cathryn spends most of her time out of the office on the trails, slopes, or by the water.

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15 Best Things to Do in Portland, Maine

By Alexandra Hall

There are plenty of things to do in Portland, Maine. But the best part: No one here is trying to impress you with trendy-this or glam-that. Sure, they want you to be here, and to share their love of creative food and a proud history of agriculture, craftsmanship, and maritime culture. At the end of the day, though what makes this proud little city fun is that the best things to do in Portland remain so true to its identity. From epic sailing trips and historic homes to funky artisanal-ware boutiques and independent locavore restaurants , these are some of the best ways to discover Old Port and beyond. 

Read on for our local-led selections of what to do in Portland.

Find our complete Portland, Maine, travel guide here .

This gallery has been updated with new information since its original publish date.

Peaks Island Arrow

Peaks Island isn’t about any one thing in particular; it’s about settling into a slower pace of life. The 720-acre island is home to about 1,000 full-time residents (which turn into 3,000 come summer) focused on maintaining the area's natural beauty, history, and laid-back living. With the ferry ride from Portland clocking in at just 15 minutes, Peaks attracts many day trippers, while others rent cottages or stay at The Inn on Peaks Island for a few days or a week or two (camping isn’t allowed). Most non-residents get around by foot, bike, or rent a golf cart on Island Avenue. To witness what makes Peaks Island such a distinctive place, do one of two must-hit activities: Walk (or bike) the loop of the island and soak up its quiet calm for an afternoon, or get yourself a seat outside at the Cockeyed Gull restaurant around lunchtime. Nothing offers a better window onto the way of life here.

Portland Schooner Co. Arrow

Boarding one of these three schooners, all of which are on the National Register of Historic Places, is a terrific and different way to see Portland. It's also fantastic for kicking back while discovering how beautiful Casco Bay is, with fresh, salty air all around you. For anyone who appreciates the above (as long as your stomach doesn't do flips on the water), consider a sail with Portland Schooner Co. your one-and-done mode of exploration. 

Portland Freedom Trail Arrow

A free and self-guided tour (no tickets required), the Portland Freedom Trail winds past 13 key sites celebrating 19th-century Black Mainers who fought to end slavery. It spotlights places along the local Underground Railroad used to secretly move formerly enslaved people into Maine and across the border to Canada (a crossing that signaled freedom). Included along the trail are other important historic abolitionist monuments, from the wharf, where many enslaved people stowed away on vessels to Maine, to churches-turned-meeting houses, private homes (with hidden passageways), and businesses that cleverly included anti-slavery pamphlets in their products.

Portland Museum of Art Arrow

Founded in 1882 as The Portland Society of Art, this is the oldest public art institution in the U.S. That said, it's relatively small and unassuming—more of a boutique museum, really. It's spread over three interconnected, architecturally significant buildings: one modern building designed by I.M. Pei; one Federal-style, three-story mansion built in 1801; and one Beaux-arts style gallery built in 1911. It’s home to pieces from giants like Andy Warhol and Claude Monet, and significant collections of paintings by Wyeth, Homer, and Edward Hopper.

Lindsey Tramuta

Lauren Burvill

Kristi Kellogg

Sarah James

Munjoy Hill Arrow

Both a jolt of energizing creativity and a window to the city's history, this neighborhood is spread across the high ground at Portland's east end. It was one of the first areas of Portland to be settled in the 1630s, and for centuries was home to working-class immigrants who made their livings on the waterfront—with an image of being a rough-around-the-edges but close-knit community. Then the ‘90s hit, along with an influx of artists and a burgeoning restaurant scene that brought new condos, art galleries, funky boutiques, and lively eateries to the area. Now, it’s also got the city's best view at the Portland Observatory , those same fun shops, and award-winning restaurants like Terlingua. It's the crossroads of historic Portland and the cool, contemporary side of the city. 

Portland Head Light Arrow

Dating back to 1791, this is the oldest lighthouse in Maine and arguably the most beautiful in New England. It contains an excellent museum (in the former Keepers' Quarters) delving into its history, as well as a gift shop. Just outside is Fort Williams Park, made up of 90 acres filled with coastal hiking paths and picnic tables, gardens, and a beach. Note that the park is open year round from sunrise to sunset, but the museum and shop are open daily in the summer, and weekends only during the off-season.

Old Port Arrow

When visitors think of Portland, it's Old Port's salty-aired, cobblestone streets and wharves that come to mind. Lined with boutiques and art galleries that alternate between posh and funky, 19th-century brick buildings, and some of the city's best restaurants and bars , it's a neighborhood that melds the cool and the quaint. In summer, Old Port is packed with tourists here for a sail with Portland Schooner Co., to check out the shops and world-famous restaurants, to visit the neighboring Casco Bay islands, or stroll the working harbor. Crowds thin out in the fall and become all but nonexistent in the winter, which is when locals reclaim the streets, and come out to dine and bar-hop themselves every evening.

Maine Day Ventures: Portland Old Port Culinary Walking Tour Arrow

The flagship among all of Maine Day Ventures’s (formerly Maine Foodie Tours) offerings is this food tour that spotlights the ever-changing group of eateries and breweries that have helped put Portland ’s working waterfront area on the map. Expect to sample everything from fresh lobster rolls to local craft beer, Maine crabmeat maki rolls, potato donuts (from Holy Donut ), and creative superfood smoothies (at Blake Orchard). Some of the included stops are expected (you simply can’t tour in Old Port without a few spoonfuls of chowder) and others surprising (chocolate truffles made from Aroostook County potatoes, for example). Above all, the storytelling and interactions are solid; guides do a good job of providing wide-ranging context for how foods are made and how they fit into the culture of the city.

Bug Light Park Arrow

Also known as Portland Breakwater Light, Bug Light (nicknamed for its small size) sits on the cusp of Portland Harbor and affords sweeping views of the city skyline. The expansive view of Portland and its working harbor dominates, with Munjoy Hill , Fort Gorges, and a handful of Casco Bay islands in the background. It's set against about nine acres of maintained and manicured parkland, which residents use for picnics, boating, fishing, and kiting. Lighthouse lovers could easily spend hours just examining the 1875 structure's decorative Corinthian columns alone.

Portland Farmers' Market Arrow

Supporting local agriculture has been a part of Maine's way of life for as long as anyone can remember, and Portland's farmers' market is one of the best places to embrace that mission. Here 40-plus growers, cheesemakers, beekeepers, berry farmers, bakers, wildflower florists, and far more set up stalls twice a week in the summer and fall (Saturdays at the Deering Oaks Park location, and Wednesdays at Monument Square) and once a week during winter (Saturdays on Stevens Avenue).

Allagash Brewing Company Arrow

The vibrant craft beer movement in Portland may not exist without Allagash. It's such a power player that the industrial park it calls home has turned into a brewery incubator of sorts, serving as a breeding ground for more than a half dozen Portland breweries , many of which have gone on to great success. The beer that made Allagash famous is its White—founder Rob Tod's version of a Belgian wheat beer—which has become the de facto light beer for IPA lovers around the country. But Allagash does many things well, and whatever your beer proclivities, you'll find something you'll enjoy here. 

Thompson's Point Arrow

Nature meets culture at this open-air entertainment venue on the Fore River, surrounded by three acres of picnic-ready lawn. The space, with its industrial-cool restored railroad shed, partners each summer with the State Theatre of Portland to host big-name concerts (everyone from Bob Dylan to Modest Mouse and The Lumineers). The rest of the year it brings in festivals: In summer, its “Maker’s Market” events are a Valhalla for those who yearn to shop artisanal, with an onsite bar in easy reach. In winter, there's a well-tended skating rink that’s part family recreational center, part all-day, grown-up party. Whatever time of year or activity you come for, don’t neglect the epicurean attractions on the periphery, either: Thompson’s Point has a long track record of luring the most incredible food trucks in Southern Maine. 

The Arts District Arrow

The Arts District is more a deep dive into the diversity of creativity in and around Portland than it is a single experience. It's a neighborhood that encourages and celebrates artistic expression—from performances on stages and sidewalks, to abstract garden sculptures in the Portland Museum of Art ; to, even, small family exhibits of paper mâché in coffee shops. Taken as a whole experience, the area is an excellent window into the kind of independent thinking that makes Portland tick, and is worth a look for anyone curious about its cultural mindset. If you can, time your trip to the first Friday of the month when, from 5 p.m. to 8 p.m., tourists and locals alike arrive to take part in First Friday Art Walk , a self-guided tour of the area's arts offerings.

Eastern Promenade Arrow

Portland’s water views are at their most glorious in this 68.2-acre historic public park, where the city harbor and Casco Bay are the backdrop to walking and running trails—wooded and paved—dog walking, to boat launches, high-energy tennis matches, picnics, and relaxed beach days. It's an easy-to-access, well-kept, splendid playground for all kinds of revelers, and one of the finest ways to experience what makes Portland such a special city.

Lucky Catch Cruises Arrow

Let the ultra-squeamish stay home; this 90-minute seafaring tour delivers a fun, hands-on understanding about one of New England's most important industries: lobstering. It's a fascinating educational mini-journey into the heart of Maine culture, and an up-close look at where one of the country's most prized foods comes from. Run by a tight-knit company of lobstermen and their friends and crew, these excursions are designed to offer a first-hand glimpse into the daily routine of catching lobster. These guys are the real deal; when not bringing passengers along, they're indeed out there on the waters, hauling in their traps. 

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32 Best & Fun Things To Do In Portland (Maine)

By: Author Jerric Chong

Posted on Published: September 2, 2019  - Last updated: October 15, 2023

You’ve probably seen Portland even if you’ve never been there.

With its jagged cliffs, crashing waves and historic white-towered lighthouses, it’s the kind of picturesque place that makes it onto all kinds of postcards.

But what if you’re looking for something a little more exciting than a photograph?

What if you’re taking a real-life vacation or honeymoon to Portland?

Here are just a few cool things to do in Portland.

They range from the outstanding to the outlandish, but they’ll all leave you with great memories of your time in Maine!

Table of Contents

1. Portland Head Light

Portland Head Light

One of the most iconic sights in Portland is the Portland Head Light .

Originally built in 1791, it’s a fully-functioning lighthouse that overlooks the Gulf of Maine, and it’s been helping sailors, soldiers and settlers reach New England since the days of yore.

You can’t miss the Portland Head Light.

It looms over the whole coastline, and it uses both a beacon and a foghorn to guide travelers through the dark.

The only difference between its past and present is that the tower has exchanged whale oil lamps for electric lights.

Today, visitors to the lighthouse can climb the stairs, see the sights, take a tour, explore the on-site museum or just lounge around the grass.

It’s a great place to suck in a deep breath and enjoy the salt and spray of the ocean.

Drop by the Portland Head Light if you’re looking for awesome stuff to do in Portland.

You’ll find it listed in just about every travel guide, and it’s worth the praise!

Address:  12 Captain Strout Cir, Cape Elizabeth, ME 04107, USA

2. Peaks Island

Peaks Island

Peaks Island is one of the best vacation spots in Maine.

Located a few miles west of Portland, it’s only accessible by a ferry ride, and it offers all kinds of fun activities for people who want to escape the crowds of the city.

Outdoor enthusiasts can rent bikes and kayaks to explore the natural scenery of the island.

History buffs can check out the lighthouses and old military bunkers that dot the shore.

Shopaholics can empty their wallets at charming little cafes, bistros and boutiques.

Peaks Island is one of those rare tourist attractions that doesn’t feel like a tourist attraction.

While it offers plenty of things to see and do, it’s still remote enough to have a quiet, peaceful atmosphere as a semi-private isle.

You should definitely check out Peaks Island if you’re looking for the best destinations in and near Portland!

3. Portland Arts District

Portland Arts District

If you’re a patron of the arts, the Portland Arts District is an absolute “must-see” while you’re in Maine.

For starters, it gathers a large number of museums, theaters, galleries and art colleges in a few square blocks.

You could spend all day exploring its performance venues, and you wouldn’t even need a car for your travels.

The Portland Arts District is also home to a tradition known as the “First Friday Art Walk.”

On the first Friday of every month, all of the art institutions open their doors to the public from 5PM – 8PM.

Many of them offer free admission or serve food and drink to guests.

It’s a great social gathering for creatives of all types, and it’s one of the best things to do in Portland on a weekend.

If you sigh every time that you see the brush strokes of “Wheatfield With Crows,” check out the Portland Arts District.

You’ll meet like-minded souls there.

Address: Congress Street, Portland, ME, USA

4. Rockin’ Horse Stables

Rockin’ Horse Stables

Woo the love of your life with a trip to the Rockin’ Horse Stables .

They offer a variety of horse-drawn rides, including carriage rides and sleigh rides, so they’re easily one of the most romantic things to do in Portland.

Winter is the best time to visit the Rockin’ Horse Stables.

With fresh snow blanketing the ground, you can cuddle close under a cozy blanket while enjoying a sleigh ride for two.

You’ll also be treated to complimentary hot chocolate when you return to the stables!

Romance can bloom in spring and summer, too.

A horse-drawn carriage ride can seem like something out of a storybook as you explore the lush green countryside.

For an extra-magical experience, you can arrange the driver to take you to a quaint little bed-and-breakfast at the end of your trip.

Visit the Rockin’ Horse Stables if you’re hoping to have a fanciful time in Portland.

They might be just what you need to get heart eyes from your boo!

Address:  245 Arundel Rd, Kennebunkport, ME 04046, USA

5. International Cryptozoology Museum

International Cryptozoology Museum

One of the highlights of downtown Portland is the International Cryptozoology Museum .

It’s the only museum in the world dedicated to rare, elusive and possibly-mythical creatures like Bigfoot and Sasquatch, and it’ll provide hours of entertainment for anyone who wants to immerse themselves in mystery.

Do you like looking at skeletons that could be yetis or mammoths?

Are you intrigued by shadowy pictures of dragons, mermaids and sea serpents?

Would you like to marvel at real-life “living fossils” of extinct species?

The International Cryptozoology Museum has it all.

Meant for both serious scholars and roadside gawkers, it’s one of the most fun things to do in Portland.

It’s also the only cryptozoology museum in the world, so it’s quite literally a one-of-a-kind attraction.

You’ll regret not checking it out!

Address:  4 Thompsons Point #106, Portland, ME 04101, USA

6. Lucky Catch Cruises

Lucky Catch Cruises

Have you ever wondered about the journey of a lobster from the bottom of the ocean to the top of a plate?

With Lucky Catch Cruises , you can watch every step of the process and eat the lobster when you’re done.

Lucky Catch Cruises will take you on a boat ride with real fishermen to bait, catch, trap and haul sea critters from the deep.

Under their careful instruction, you can get your hands dirty like you’re part of the crew.

Once you’ve caught some good lobster, you can purchase them for a wholesale price and take them across the docks to a special seafood restaurant that will cook your prize for you right then and there.

You can’t visit Maine without indulging in some fresh-caught lobster, and nothing is fresher than a lobster that you catch yourself.

Book a tour with Lucky Catch Cruises to learn the true meaning of working for your dinner.

Address:  170 Commercial St, Portland, ME 04101, USA

7. Coastal Maine Botanical Gardens

Coastal Maine Botanical Garden / JR P / flickr

The Coastal Maine Botanical Gardens are about an hour north of Portland, so you’ll need to be willing to make a road trip to see them, but they’re definitely worth the fuel.

They’re so gorgeous that they’ve attracted visitors from more than 63 countries, and they’re considered one of the top attractions in the whole of New England.

Why are the Coastal Maine Botanical Gardens so special?

It starts with a huge, sweeping landscape that goes on for miles.

You can find everything from hushed forests to noisy ponds filled with fish that literally leap through the air.

They also offer a lot of fun attractions for visitors.

Take a boat tour; walk through the butterfly house; visit the cafe and souvenir shop.

There are always neat things to do in the gardens.

Maine is one of the most beautiful states in the U.S. , and when you’re watching the sunlight play off the rustling leaves of the Coastal Maine Botanical Gardens, you’ll understand why it gets this distinction.

Put it on your list of Portland attractions if you want to be awed by the beauty and tranquility of nature.

Address:  132 Botanical Gardens Dr, Boothbay, ME 04537, USA

8. Commercial Street

Commercial Street / Corey Templeton / flickr

There’s nothing like the smell of the sea as you stroll near the water’s edge.

Throw in all kinds of shops, bars, pubs, boutiques and restaurants, and you’ve got the greatest tourist destination in Portland!

Running right along the bay, Commercial Street is one of the liveliest places to visit in the city.

There are always people weaving around each other, especially near the wharves and docks.

Not only do these locations offer great views of boats docking and fishermen calling out their hauls, but they’re also lined with everything from seafood restaurants to customized t-shirt shops.

There’s always something new to experience!

If you prefer not to mist yourself with sea spray, wander towards the historic side of Commercial Street and enjoy the old-world charm of colonial buildings and cobblestone streets.

It’s a great taste of vintage New England, and you can take in lots of landmarks during your stay.

Stop by Commercial Street if you’re looking for fun things to do in Portland.

It’s one of the quintessential destinations in the city, so you won’t want to miss it!

9. Maine Foodie Tours

Maine Foodie Tours

When your stomach is rumbling after a long day of travel, you’ll need some tasty treats to help you refuel.

Maine Foodie Tours can help.

While not the only company of its kind, Maine Foodie Tours has made a name for itself as one of the best.

It offers award-winning tours that are centered around specific foods, themes, locations and events.

For example, the “Old Port Lunchtime Lobster Crawl” will leave your fingers permanently covered in butter after you’ve cracked open the most delicious lobster tails in the area.

Also, the “India Street Food Artisans” will keep your taste buds ablaze from the spices of the east.

Give a call to Maine Foodie Tours if you’re wondering what to do in Portland.

Everyone has to eat, but you don’t have to sustain yourself on fast food scarfed down in a hotel room.

You can take your culinary experiences to the next level with a proper food tour.

Address: 227 Commercial St, Portland, ME 04101, USA

10. Eastern Promenade

Eastern Promenade

If you’re traveling on a budget, you could probably use some free things to do in Portland.

Fortunately, Eastern Promenade is so much fun that you’ll marvel at the fact that it doesn’t cost a dime!

The Eastern Promenade has lots to offer to visitors.

If you like working up a sweat, you can play a game on the baseball, basketball or tennis courts.

If you enjoy sightseeing, you can visit on-site landmarks like the old railway or the mass grave of American soldiers lost in the War of 1812.

Being on the waterfront, the Eastern Promenade is also a popular spot for picnics, so there are always blankets spread on the grass and kids playing in the distance.

There are plenty of free things to do around Portland. You just have to find them.

The Eastern Promenade can be the first thing on your list, but leave some room for others as well!

Address:  510 Eastern Promenade, Portland, ME 04101, USA

Exploring other parts of Maine? Why not check out some of the things to do in Bar Harbor ?

11. The Maine Mall

The Maine Mall

The Maine Mall lives up to its name by being the largest shopping complex in the state.

In fact, it’s so gargantuan that it’s the second-largest in the whole of New England.

It boasts more than 100 stores while covering 1.1 million square feet of retail space.

You’ll definitely be able to stop until you drop at the Maine Mall.

From luxury stores to cheap kiosks, it has a little bit of everything.

A food court will keep you from going hungry as you burn off the calories by power-walking through the corridors.

Another great thing about the Maine Mall is that it hosts special events throughout the year.

Depending on the timing of your vacation, you might be able to catch a musical performance, book signing, holiday festival or food truck battle.

The Maine Mall is one of the best things to do in Portland when you have a little money to spare.

How often do you get the chance to buy shoes and eat bonbons at the biggest shopping complex in Maine?

Take advantage of the opportunity while you can!

Address:  364 Maine Mall Rd, South Portland, ME 04106, USA

12. Palace Playland

Palace Playland Amusement Park

Located a few miles south of Portland in a place called Old Orchard Beach, Palace Playland is known as “Maine’s only beachfront amusement park.”

Its rides directly overlook the water, so when you’re screaming on the roller coaster or relaxing on the Ferris wheel, you’ll be doing it with incredible ocean views!

There are other things to enjoy at Palace Playland as well.

It offers games, slides, carousels, bumper cars, kiddie pools and fun houses.

An arcade is filled with photobooths and skeeball lanes.

Your favorite concessions are sold at dozens of snack stalls.

If you’re looking for the best Portland attractions, consider Palace Playland.

You could whittle away entire weekends with all of its games and amusements, and you’ll never get another view like the one atop its gigantic rides!

Address:  1 Old Orchard St, Old Orchard Beach, ME 04064, USA

13. Standard Baking

Standard Baking / Corey Templeton / flickr

To enjoy Portland like a local, you’ll need to know all of the local points of interest.

One of them is Standard Baking .

Found behind an unassuming shopfront, Standard Baking is one of the best bakeries in the city.

It offers everything from chewy fudge squares to soft cinnamon rolls dripping with icing.

Everything is made fresh with the sunrise, and you can often smell the bakery from outside long before it opens its doors.

The only bad thing about Standard Bakery is that it’s considered a hot spot in Portland, so the lines can get long.

This is especially true in wintertime when its warm desserts and cocoas are in high demand.

Once you bite into the flaky layers of a bichon au citron, however, you’ll understand that Standard Baking is worth the wait.

It’s so good that we consider it one of our top 10 places to visit in Portland.

No other bakery gets this honor, but Standard Baking is just too delicious!

Address:  75 Commercial St, Portland, ME 04101, USA

14. Maine Narrow Gauge Railroad Museum

Maine Narrow Gauge Railroad Museum / Paul VanDerWerf / flickr

Did you collect trains as a kid?

The Maine Narrow Gauge Railroad Museum will be a little like your childhood dreams coming to life.

Located on a functioning narrow-gauge railway, the Maine Narrow Gauge Railroad Museum offers an experience that’s both interesting and educationally engaging.

You’ll learn about the history of the railway, but you’ll have fun while you’re doing it.

You’ll be able to take a tour, climb aboard the cars, press controls in the caboose and even ride on the tracks for a three-mile journey down the waterfront.

The Maine Narrow Gauge Railroad Museum is a must-do in the Portland area.

Not only is it a fascinating attraction, but it’s specific to the railways of the city, so you can’t find anything like it anywhere else in Maine.

Address:  58 Fore St, Portland, ME 04101, USA

15. Fort Gorges

Fort Gorges

Fort Gorges is an abandoned military fortress off the shores of Casco Bay.

It doesn’t offer tours, and it’s only accessible if you boat, canoe, kayak or hire a water taxi to get yourself there.

It’s recommended that you bring a flashlight if you want to explore the darker parts of the ruins.

There are no guarantees of safety if you reach a crumbling deck or overgrown bunker wall.

If this sounds like the perfect adventure for thrill seekers, you’re absolutely right!

Despite its fearsome reputation, Fort Gorges is a popular tourist attraction in Portland.

It’s such a cool and unique thing to do that it draws visitors like a moth to a flame.

It isn’t that scary, either.

On sunny days, it can even become a family-friendly place if the kids want to play or picnic on the grass outside of the fort.

Just make sure that you bring that flashlight if you really want to excavate something from the ruins.

Fort Gorges is an entirely self-guided attraction, and this can mean both good and bad things for Portland vacationers.

Address:  Portland, ME 04101, USA

16. Munjoy Hill

Munjoy Hill

Known to locals as “the Hill,” Munjoy Hill is one of the trendiest neighborhoods in Portland.

It used to be a rougher, more working-class place, but it gentrified in the ’70s and ’80s, and today’s residents are young hipsters who bring vibrant energy to its bustling streets.

You’ll find all of the latest trends in Munjoy Hill.

If everyone is going crazy over a bubble tea, it originated from a Munjoy Hill cafe.

If everyone is eager to get a job at a new start-up, it’s housed in a Munjoy Hill loft.

Despite its reputation as an expensive place, there are free things to do in the neighborhood.

It runs along the waterfront, so you can enjoy great views from its parks and observation points.

It’s packed with businesses, so there are always special deals, events and giveaways.

You might not want to live around Munjoy Hill, but in terms of fun places to visit, it deserves to be on your vacation itinerary.

You should experience Munjoy Hill at least once while you’re in the city.

Address: Portland, ME 04101, USA

17. Crescent Beach State Park

Crescent Beach State Park / Wally Gobetz / flickr

Despite its proximity to the water, Portland isn’t really considered a “tropical” location.

Its beaches are usually too cold or too rocky to attract the bikini crowd.

That said, there are still a few places where you can go to enjoy sand and sun, and one of them is Crescent Beach State Park .

Crescent Beach State Park stretches for almost 250 acres across southern Maine.

It offers beaches, playgrounds, fields, groves and nature trails.

There are places to lay down a towel and work on your tan; there are places to swim, hike, fish, kayak, picnic or wade into tide pools and pick up starfish.

If you’re traveling there in the wintertime, there are even slopes where you can go skiing!

Crescent Beach State Park has a little something for everyone, so it’s definitely one of the best Portland attractions on the map.

If you’re looking for the most tropical vacation that you can have in Maine, Crescent Beach is the place to be.

Address:  109 Bowery Beach Rd, Cape Elizabeth, ME 04107, USA

18. Merrill Auditorium

Merrill Auditorium / University of Southern Maine School of Music / flickr

If you like a show, you’ll love Merrill Auditorium .

It’s one of the most popular venues in Portland, and it hosts everything from concerts to theater productions within a vintage, turn-of-the-century building with a gigantic pipe organ as its centerpiece.

One of the most anticipated acts of the Merrill Auditorium is the Portland Symphony Orchestra.

There’s also the Portland Ballet and the Friends of the Kotzschmar Organ.

During the holidays, the city’s famous Polar Express is co-organized by the auditorium.

You can even rent Merrill Auditorium for your own events.

For example, if you’re marrying or honeymooning in Portland, you might like the classically romantic architecture as a backdrop for your wedding portraits.

One thing is for sure: The Merrill Auditorium is the beating heart of the arts and culture scene in Portland.

If you want to enjoy any kind of show in the city, you’ll probably wind up here.

Address:  20 Myrtle St, Portland, ME 04101, USA

19. Deering Oaks

Deering Oaks Park

Deering Oaks is a nice park in Portland.

There are fields, ponds, playgrounds and ball fields for visitors of all ages, and seasonal activities like ice-skating will keep you occupied at any time of year.

The best thing about Deering Oaks, however, is the fact that it’s a bustling venue for all kinds of Portland events.

Every time that you venture into the park, there’s something new going on.

There might be a farmer’s market on Thursday and a movie festival on Friday.

There might be guided nature walks at sunrise and bachata dance classes lighting up the lamp posts at night.

If you’re wondering what to see and do in Portland, you might appreciate the fun roster of activities at Deering Oaks.

The sheer range of them transforms Deering Oaks from a regular public park into one of the major points of interest of Portland.

Address:  Park Ave, Portland, ME 04101, USA

20. Portland Observatory

Portland Observatory / Corey Templeton / flickr

The Portland Observatory is a rare sight.

Not only is it a unique structure in Maine, but it’s also the last surviving tower of its kind in the entire United States.

Everything about it has become a relic of the past.

What is the Portland Observatory?

Simply put, it’s an old-fashioned signal tower.

It used both telescopes and flags to help ships reach the local wharf throughout the 19th and 20th centuries.

Today, the Portland Observatory has been converted into a maritime museum where visitors can learn about its history and heritage.

You can even climb to the top of its 86-foot tower and enjoy scenic views of the land, water and sky.

On clear days, you can see all of the way to Mount Washington!

Now that’s a sightseeing opportunity that you don’t want to miss!

Address:  138 Congress St, Portland, ME 04101, USA

21. Bedrock Gardens

Bedrock Gardens

If you love nature but get tired of the same dirt-and-rock nature trails that wind through every state park, you might like Bedrock Gardens .

It’s a horticultural sanctuary that emphasizes art just as much as nature, so it’s a fun destination for people who enjoy new experiences.

The landscape of the garden is beautiful.

There are flowers, trees and streams as far as the eye can see, and there are plenty of pavilions and pagodas if you want to take a break in the shade.

The best part of Bedrock, however, is its art.

In addition to the usual fountains and statues, there are also gates, groves, birdhouses and all kinds of homemade sculptures made from metal and fabric.

Everything is uniquely crafted and displayed, so you’ll feel like you’re looking at real art made by real people.

If you’re wondering what to do in Portland on a dull afternoon, you can add some serious interest to your day with a trip to Bedrock Gardens.

It offers a lot of cool things to see, catalogue and photograph, so it’s perfect for people who aren’t afraid to wander off the beaten path.

Address:  19 High Rd, Lee, NH 03861, USA

22. Portland Museum of Art

Portland Museum of Art

This museum is part of the Portland Arts District, so if you’ve already marked off a weekend for exploring the bounds of West End, you can skip this part of the list.

If you’re pressed for time, however, or if you’re looking for the absolute best things to do in the arts district, the Portland Museum of Art should be your number one stop.

As the oldest art institution in Maine, the Portland Art Museum has been serving art and culture to the locals since 1882.

Rather than being housed in a single building, it’s actually comprised of three buildings that are joined together with a common purpose, and they boast more than 17,000 paintings and artifacts all together.

Art lovers, you won’t want to miss the Portland Museum of Art.

It’s the central hub of the whole Portland Arts District, and it’s one of the best things to do in all of Maine.

Don’t vacation in the state without stopping by its top attraction!

Address:  7 Congress Square, Portland, ME 04101, USA

23. Old Port

If you like the thought of strolling near the waterfront with a cold drink in hand and your flip-flops slapping against the cobblestones, check out the Old Port.

It’s one of the biggest tourist attractions in Portland, and it’ll offer an entertaining day trip for visitors of all ages.

Activities at the Old Port range from exciting ferry rides to leisurely food tours.

You can eat, drink, shop or just people-watch along the harbor.

It’s the kind of place where street musicians always have their hats on the ground and crowds line up for hours at their favorite crab joints.

Maybe you’re looking for a nice hotel during your romantic honeymoon.

Maybe you just want something to do on a sunny day in Portland.

Whatever your reasons for checking out the Old Port, it can provide a good time that you’re looking for, so pack up your swimsuit and get moving!

Address: Commercial St, Portland, ME 04101, USA

24. Greenbelt Walkway

Greenbelt Walkway / Corey Templeton / flickr

The Greenbelt Walkway is a five-mile trail that will take you through some of the most beautiful parts of Portland.

You can walk, jog, skate or bike it, and best of all, it won’t cost you a cent.

One of the coolest things about the Greenbelt Walkway is the fact that the landscape changes as you venture further and further down the trail.

You’ll be transported from grassy fields to swampy wetlands to sandy beaches, so your eyes will always be able to feast on new and breathtaking sights.

Another nice thing about the Greenbelt Walkway is that it offers different things to do along the way.

You can take a side trip to one of the parks or landmarks for further sightseeing, or you can venture into one of the many local shops, cafes and restaurants if you need a blast of air conditioning on a hot day.

The Greenbelt Walkway is one of the best free things to do in the city of Portland, so it’s worth a marker on your map.

Maine has lots of beautiful, natural destinations, and a place like the Greenbelt Walkway will let you see them all along a single trail.

Address: Bug Light Park, South Portland, ME, USA

25. Odyssey Whale Watch

Odyssey Whale Watch

Maine has some of the best shores in the world for whale-watching, and Odyssey Whale Watch will let you get up close and personal with these majestic mammals.

The adventure starts when you board a small vessel known as the Odyssey.

It isn’t a luxury liner, but it’s comfortable, and its petite size will let its captain maneuver you closer to the whales.

While you’re waiting for them to appear, you can enjoy snacks, soft drinks or alcoholic cocktails.

You can gaze at the water as a romantic tryst or snap some commemorative photos with amazing waves as the background.

When the whales appear, the wait will be worth it.

You’ll be so close to them that you can count the water droplets on their backs!

Getting to observe these amazing animals in the wild is one of the top things to do in Portland, so don’t be afraid to call Odyssey Whale Watch and book a tour today.

SPACE is an art and performance venue in Portland that delights in the unique.

Its specialty is experimental, contemporary art, so it’s always on the lookout for fun, fresh, colorful and offbeat things.

Do you like supporting local artists?

SPACE holds plenty of fundraisers, and they often intersect with films, lectures and gallery showings.

Do you enjoy going to classes and workshops where you can learn new things?

SPACE has plenty of events on its weekly calendar.

Whether it’s a film festival for silent movies or a poetry slam in a hallway filled with hand-painted watercolors, there’s always something different going on at SPACE.

You should give it a try if you’re the kind of person who’s willing to live outside of the box.

Address:  538 Congress St, Portland, ME 04101, USA

27. Bubba’s Sulky Lounge

Bubba’s Sulky Lounge

Dust off your collar dresses and low-heel flats!

Bubba’s Sulky Lounge is here to take you back to the ’60s with its retro architecture and eclectic playlists.

There are many nightclubs in downtown Portland, but Bubba’s Sulky Lounge uses its vintage theme to stand apart from the rest.

Buzzing lights will flash in neon colors over your head, and a tiled rainbow floor will look like something straight out of the disco movies of yesteryear.

There are regular costume parties and other old-school throwbacks.

As for its drinks, you’ll be able to enjoy all kinds of special cocktails from both the past and the present.

There are also double dance floors, so when you get too sweaty on the first one, head to the second and keep the party going.

Bubba’s Sulky Lounge is one of the best destinations in downtown Portland, so if you’re looking for ways to cut loose on a lively evening, don’t hesitate to hit it up.

The tights are optional. The only requirement is to have a blast.

Address:  92 Portland St, Portland, ME 04101, USA

28. Bug Light Park

Bug Light Park

Despite the name, you won’t be disturbed by any bites or stings at Bug Light Park .

It gets the moniker from the short, squat lighthouse that overlooks its waterfront.

Maine is no stranger to lighthouses, so it takes something special for them to stand out, and that’s exactly what the quaint little “bug light” does.

Of course, the lighthouse isn’t the only attraction at Bug Light Park.

There are many places to see and explore.

The windy, grassy fields are great for kiting, and the piers are a local hot spot for saltwater fishing.

There’s also a liberty ship memorial on the far end of the park that houses the remnants of a WWII vessel.

You’ll enjoy Bug Light Park if you’re looking for a peaceful place to spend an easygoing afternoon.

Portland vacations don’t have to be jam-packed with tourist attractions to be exciting.

Sometimes, a little R&R is the most enjoyable part of a getaway.

Address:  South Portland, ME 04106, USA

29. The Allagash Brewery

Allagash Brewing Company

Famous for its Belgian-style beers, the Allagash Brewery can be considered one of the top tourist attractions in Portland.

You don’t even have to be a big drinker to enjoy it.

It has enough history to offer an engrossing look into the general brewing customs of New England.

For example, did you know that many of Portland’s beers were aged in oak barrels until modern machines came along?

The Allagash Brewery still uses wooden barrels for some of its specialty beers.

This is just one of the fascinating facts that you can learn with a tour of the brewery.

Of course, drinkers will probably enjoy the tour more than non-drinkers.

There’s nothing like free samples to give you a nice buzz!

No matter where your alcohol tolerance lies, however, you’re guaranteed to have a good time at the Allagash Brewery.

It’s a chance to see how your favorite craft beers are made while you sip on the fruits of the labor that you’re witnessing before you.

Who wouldn’t be intrigued by that?

Address:  50 Industrial Way, Portland, ME 04103, USA

30. Fore River Sanctuary

Fore River Sanctuary / Corey Templeton / flickr

Home to Jewell Falls, the only natural waterfall in Portland, the Fore River Sanctuary is a great place to get away from it all.

Its most stunning feature is its rugged natural beauty.

The Fore River Sanctuary offers gorgeous landscapes that haven’t been touched or tempered by man.

You can really breathe there in a way that you might not be able to when you’re jostling elbows with every Tom, Dick and Harry in the city.

It’s so quiet at the sanctuary that you can hear every rush of water over the rocks and every note of the birds in the trees.

Another great thing about the Fore River Sanctuary is that it’s still accessible to visitors despite its natural landscapes.

It has modern conveniences like benches and bathrooms, and you can follow signs along the trails to keep yourself from getting lost.

You won’t have to act like a complete caveman while you’re there!

All things considered, however, the Fore River Sanctuary is one of the more rugged parks in Portland, so it should definitely top your list if you’re looking for authentic things to do in Maine .

Address:  157-169 Rowe Ave, Portland, ME 04102, USA

31. Mackworth Island

Mackworth Island

Mackworth Island is one of the many islands in the waters of Casco Bay.

However, it distinguishes itself from the rest by offering cool things to do that you can’t find on the other isles.

For example, there are a lot of legends about fairies on Mackworth Island.

It’s a heavily wooded area, so it’s easy to imagine tiny winged creatures darting among the trees and ravines.

There’s even a “Fairy Village” that lets you construct your own wood-and-metal fairy house and leave it for future visitors to find.

If you’re planning a trip to the city, Mackworth Island is worth the quick trip across the bridge.

It’s only a few miles from downtown Portland, so it isn’t like you have to go on a long voyage to get there, and you’ll get to partake in some fun and unusual hobbies while you’re visiting.

There are definitely worse ways to spend a weekend in Maine!

32. Len Libby Chocolates

Len Libby Chocolates

Have you ever seen a 1,700-pound chocolate moose?

Is that something that you’d like to cross off your bucket list?

Is that something that you’d like to add to your bucket list?

Len Libby Chocolates is a candy shop located a short drive from Portland.

Despite the name, it offers all kinds of sweet treats that aren’t derived from cacao beans; you can find taffy, truffles, twinkies, gummies, nuts and many other snacks.

There’s even an ice cream parlor if you’d like to add your sweets to the top of a hot fudge sundae.

The biggest attraction of the shop, however, is its life-sized chocolate moose.

His name is Lenny, and he’s one of those roadside attractions that you just have to see to believe.

Stop by Len Libby Chocolates if you’re ready to take some pictures that your friends and family will boggle at for years to come!

Address:  419 US-1, Scarborough, ME 04074, USA

Start Planning Your Trip To Portland

These are just a few of the best things to do in the city of Portland.

It isn’t a coincidence that it’s one of the most highly-traveled and highly-regarded parts of Maine!

If you’re ready to experience the magic for yourself, let these suggestions be your guide for a great trip to Portland.

Best Hotels

Top Restaurants

Portland's Best Bars

Top Breweries

Day Trips From Portland

Things to Do in Maine

Things to Do in Bar Harbor

Things to Do in Bangor

Maine's State Parks

Whale Watching in Maine

Beach Destinations

Food to Try in Maine

Best Places to Eat Lobster

Guide to Acadia

Things to Do

How to Visit in a Day

Best Time to Visit

Weather & Climate

Portland International Jetport Guide

Top Things to Do

16 Best Things to Do in Portland, Maine

This small but sophisticated coastal city has tons to offer

cfwphotography / Getty Images

As northern New England's cultural hub, Portland, Maine, has become a showcase for artists, musicians, craftsmen, and actors. This charming coastal city routinely appears on lists of America's best places to live, visit, dine, and play outdoors, and is also an increasingly popular port of call for cruise ships. Portland and nearby towns in southern Maine are also a mecca for outdoor enthusiasts and fans of spectacular scenery.

If you're looking for memorable things to do, here's your guide to some of the best attractions in Portland and southern Maine.

Shop Local at the Portland Farmers' Market

The Portland Farmers' Market is more than just a place to buy produce. It's a historical pillar of the community, having originally started in 1768 (eight years before the Declaration of Independence was signed). The Farmers' Market takes place year-round, so you can shop regardless of what month you visit. It takes place outdoors at Deering Oaks Park from the end of April until December every Saturday and Wednesday, but moves to a nearby indoor location during the winter months and only opens on Saturdays. There's perhaps nowhere better in the state to purchase organic fruits and vegetables, locally-made honey, freshly made goat cheese, or bustling bouquets of wildflowers.

Enjoy the Outdoors at Eastern Promenade

Few city parks offer the seaside views that you can find at Portland's Eastern Promenade . This 68-acre public park completely envelopes the East End peninsula, offering sweeping views of Casco Bay and the islands just off the coast. Easily accessible from downtown Portland and just a mile from the Old Port, this park offers visitors much more than just a scenic stroll. At the south end of the Promenade, Fort Allen Park delights history lovers with artifacts dating back to the Revolutionary War. Birdwatchers camp out near the shoreline to catch a glimpse of the over 200 bird species that reside in the local area. If you're visiting in the warmer months, take a dip in the bay or rent a kayak; if it's winter, pick up a sled and take advantage of the snow-covered bunny slopes.

Imbibe at a Craft Brewery

Allagash Brewing Company / Flikr / CC BY 2.0 

Portland has gained a reputation as one of the premier craft beer hotspots in the United States, and while there are a number of brewery options to try, none of them are more well-known than Allagash Brewing Company . Founded in 1995, Allagash exploded into the craft beer scene with their Belgian-style Allagash White, which is served on tap at bars across the country. You can take a tour of the brewery and stop by their on-site bar to try some of their products that are only offered at the brewery and no where else.

Allagash is a favorite for tourists and locals alike, but beer lovers shouldn't ignore the other superb breweries in town. Lone Pine is centrally located next to East Promenade Park and Oxbow Beers is also conveniently situated in downtown Portland.

Catch Your Own Lobsters

Want to taste the freshest lobster of your life? Catch it yourself! In Portland, you can board an authentic lobster boat with real Maine anglers and venture out into scenic Casco Bay, where you'll learn how to bait and haul traps. Lucky Catch Cruises depart from Long Wharf several times daily from the first weekend in May through the last weekend in October. The luckiest part of your adventure is the opportunity to buy the lobsters you caught at discounted, wholesale prices. Portland Lobster Company , located across the street from the dock, will cook your catch and supply the butter.

Photograph the Iconic Lighthouses

TripSavvy / Christopher Larson 

The Maine coast has more than its fair share of New England's lighthouses, and when you visit the state's largest city, capturing your own images of storied Portland Head Light should be on your must-do list. George Washington was president when a beacon was first constructed on this dramatic ledge. There's a museum in the former keeper's quarters, built in 1891, that you'll want to visit. It's open daily from Memorial Day through October and on a more limited schedule starting in late April and through the end of December. Allow plenty of time to explore historic ruins in adjacent Fort Williams Park.

There are five more lighthouses within an easy drive from Portland, from Breakwater Lighthouse in the north to Two Lights State Park in the south, so make a day of photographing these inspiring guardians of the Maine coast.

Visit the Portland Museum of Art

View the outstanding collection of American, European, and contemporary paintings and other works at the Portland Museum of Art , Maine's largest and oldest public art museum. In addition to its permanent collection, which includes many Maine masterworks among its highlights , the museum hosts special exhibitions and events throughout each year. Winslow Homer's restored studio is the museum's most unique holding. Reserve a spot on a small group bus tour to this landmark in Prouts Neck, Maine, where you'll see scenes that inspired Homer's dramatic marinescapes.

Shop at the Old Port

This seaport city's waterfront warehouses and cobbled streets that mariners have trod for centuries now beckon to shoppers. Downtown Portland's Old Port District has been reimagined as a retail hub, and you'll delight in exploring shops and galleries with distinctly Maine flair. Don't miss Sea Bags , where the totes are made from recycled sails. And be sure to stop into Harbor Fish Market , even if it's only to drool over the bounty of Maine's waters.

Sightsee from a Fire Truck

Climb aboard an antique fire truck for a memorable look at Portland's neighborhoods and attractions. Portland Fire Engine Co. offers the city's coolest tours, narrated by locals who not only share historical tidbits but the inside scoop on a city they love. In just under an hour, you'll have a good feel for the city. The fire truck stops for photo ops and a multimedia presentation adds to the experience. Tours depart from Commercial Street in front of the Portland Lobster Company from late April through late October.

Embark on an Island Cruise

Hundreds of isles dot Portland's storied waters, and Casco Bay Lines provides ferry service to the major islands. Far more than a year-round transportation company, the ferry line's schedule includes scenic cruises including sunrise and sunset excursions and music cruises featuring local bands and dancing. One of your best options is the 15-minute voyage to Peaks Island, where you can rent a bike and find quiet beaches, casual dining and one of Maine's quirkiest attractions: the Umbrella Cover Museum . Casco Bay Lines is also famous for its mailboat runs . That's right: You can see the sights as this working boat delivers island dwellers' mail.

Tour Historic Homes

Portland is an architecturally interesting city, which was largely rebuilt in Victorian style following a devastating 1866 fire . One of the city's first brick buildings not only survived the blaze, but it also became Maine's first historic house museum in 1901. If you're a literature fan, you'll want to be sure to tour the Wadsworth-Longfellow House , where influential poet and famous Portland son Henry Wadsworth Longfellow spent his childhood.

For a glimpse of lavish living in the city, visit another Great Fire survivor. Step back into the Victorian Age on a guided tour of the beautifully furnished Victoria Mansion , which was the most expensive home ever built in Maine at the time it was completed in 1860. Both houses are open for tours May through October. Victoria Mansion also reopens for special holiday tours from late November through early January .

Indulge in a Food Tour

Portland is Maine's top culinary destination, and there are so many restaurants, bakeries, breweries and gourmet food producers competing for your stomach space, you may find choosing where to dine and imbibe your trip's biggest dilemma.

Enter Maine Foodie Tours : their Portland walking tour is an efficient way to sample some of the Old Port's most delicious dishes and treats. Over the course of three hours, you'll taste everything from chowder to chocolate truffles made with Maine potatoes and sip craft beer and Maine honey wine along the way. Plus, your guide will share an insider's perspective on the food scene that will help you plan meals for the rest of your stay. Small group tours leave from the Old Port Wine Shop on Commercial Street year-round.

Explore a Cemetery

Portland's Eastern Cemetery dates back to 1668, but in modern day, is brought to life by devoted guides during Spirits Alive tours available Wednesday, Thursday, Saturday or Sunday from July through mid-October. Once neglected and badly vandalized, this historic landscape has been resuscitated and transformed into a city attraction. You'll especially appreciate the artistry of 700 headstones etched by local stonecutter Bartlett Adams. If you're visiting Portland during the Halloween season, don't miss your chance to Walk Among the Shadows , bumping into ghostly storytellers.

Behold a Guinness World Record Holder

Just outside of downtown Portland in Yarmouth, Maine, there's a free attraction that will allow you to say you've seen the whole world in a day. Eartha is the world's largest revolving globe, and as this marvel spins, you'll feel a new appreciation for Maine's place on the planet. Eartha occupies the lobby of Garmin, which purchased the massive globe's innovative creator: DeLorme. A condition of the sale was that Eartha ​remains open and free to the public. You can visit any weekday year-round.

Find a Hidden Bar

Psst! Want to hang out at a cool speakeasy while you're in Portland? Make sure you have cash on you because that's all they accept at Lincolns , where all drinks cost a Lincoln. That's a $5 bill: Get it? Dimly-lit and with a local vibe, this basement bar has a secret entrance at 36 Market Street, and once you find it, whatever you do: Don't photograph it. Comedy and open mic nights are the best times to go. If it's your first time trying to find your way in, an Uber driver may be your best tipster.

Wow Your Kids at a Museum or Planetarium

Treat wee ones to a memorable adventure at the Children's Museum and Theatre of Maine in Portland, where hands-on exhibits—including a lobster boat, farmers' market, space shuttle, ranger station, and tide pool touch tank—will fascinate and entertain them. There are even dedicated areas for toddlers, so it's the perfect first museum experience for the tiny set. Take in a spectacular star show or laser light display at the University of Southern Maine's Southworth Planetarium , too, and you'll be as enthralled as your children.

See a Theater Performance

If you're a theater fan, you'll want to see what's on at Portland Stage . Maine's largest professional theater company produces seven mainstage shows annually and also stages new and experimental works and hosts talks and other events. The Portland Players , Maine's oldest community theater company, also presents engaging performances during a season that includes drama, comedy, and musicals. Check the schedule at John Lane's Ogunquit Playhouse , too. This summer theater venue, located south of Portland in Ogunquit, is renowned for its high-quality Broadway musicals.

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15 Best Things To Do In Portland, Maine

Portland is undoubtedly Maine’s most exciting city, and with stunning coastal scenery, lighthouses, an incredible culinary scene, and historic New England charm, it’s easy to see why. 

Located in the southern region of the state, Portland is accessible from so many other parts of New England, making it easy to see while visiting this region. It also makes for a perfect homebase while you explore different areas of coastal Maine, or a worthwhile pitstop on your way to Acadia National Park. 

This post shares all the very best things to do in Portland, Maine to help you plan the perfect itinerary. Whether you’re planning a day trip, or a few nights here, these are the best things to check out in this beautiful New England city.

Where To Stay In Portland, Maine

The best area to stay in Portland is the Old Port district of downtown. This is also the most scenic area of the city, and you’ll find historic cobblestoned streets, beautiful alleyways along the waterfront, and lots of shopping and dining options within walking distance. Some recommended hotels in the Old Port neighborhood are:

• The Press Hotel
• Portland Harbor Hotel
• Hyatt Place Old Port

If you’re on a budget, the cheapest area of the city to stay in is South Portland, which is just a 15-minute drive to Old Port. You’ll find a lot of hotel chains in this area with much cheaper prices, and you’ll also be closer to the lighthouses.

Recommended hotels in South Portland:

• Holiday Inn Express & Suites
• Courtyard By Marriott Portland Airport

Best Things To Do In Portland, Maine

1. see the lighthouses.

You most definitely can’t leave Portland and not see the lighthouses! Portland is home to New England’s most famous and photographed lighthouse, Portland Head Light, and if you just see one lighthouse during your visit, this is the one to see.

Portland Head Light is inside Fort Williams Park on Cape Elizabeth and is surrounded by a dramatic, rocky coastline that makes for epic photos to remember your trip by. There’s a paved path that goes around the park that offers different vantage points of the lighthouse, and you can also walk right up to it for a unique perspective. 

If you have time, it’s also worth visiting the other two lighthouses nearby: Spring Point Ledge Light, and Bug Light. While these lighthouses are much smaller than Portland Head, they’re both still very fun to visit and offer beautiful views of the water. 

Visiting the lighthouses does require a car, but if you’re visiting without one, consider taking a tour around the city, which also includes Portland Head Light .

If you want to see all three lighthouses without a car, the best option is to hop on a boat tour, which departs right from downtown Portland. The Lighthouse Lovers Cruise tour is 60 minutes long, and passes by all of Portland’s lighthouses:

2. Walk The Streets Of Charming Old Port

Portland’s most photogenic area is definitely Old Port, and you’ll want to be sure to spend at least a few hours exploring the charming streets of this neighborhood. As the city’s oldest and most historic area, it also perfectly balances old-world charm and the city’s rich maritime legacy.

Many of the restaurants and boutiques in this neighborhood are housed in historic warehouse buildings, and you’ll find hidden alleyways along the harbor with bobbing fishing boats and lobster traps for an authentic New England experience. 

3. Take A Boat Tour Of Casco Bay

One of the best ways to enjoy Portland is by taking in views of the city by boat, which also offers opportunities to see the surrounding Casco Bay. 

There are a few fantastic tours that depart right from Old Port, and one of the best ones is this Harbor Lights and Sites tour, which passes by the lighthouses, and the islands around Casco Bay:

A memorable boat tour to take in Portland is this 2-hour Tall Ship Cruise around the bay. Your guides on this tour will help you spot seals and other wildlife in the water, and you’ll also have the opportunity to learn how to sail and hoist the sails if you’re up for it. Sailing vacations are full of benefits , so give it a try!

If you’re visiting between November and April, most boat tour companies are closed for the season, but you can hop aboard the Casco Bay Island Ferry, which is one of the best things to do in Portland, Maine in the winter . The Casco Bay ferry line is also very affordable, so if other tours aren’t in your budget, this is a great option. 

Visitors are welcome to hop aboard just to cruise around, and round-trip fares start at around $8.  

4. Take A Food Tour

Portland is one of New England’s most exciting culinary destinations , and it can be overwhelming to decide where to eat. To help you hone in on the best places to start and get a taste of New England cuisine, definitely consider booking a food tour of the city.

The Old Port Culinary Walking Tou r takes you through some of the best parts of the neighborhood and stops at up to 7 eateries along the way to sample a variety of foods. 

Craving something a bit sweeter? You’ll want to book an Old Port Donut Walking Tour! This tour allows you to skip the line at Portland’s most famous donut shop, The Holy Donut, and also sample donuts at two other locations. 

5. Eat Fresh Seafood

After your food tour, you’ll want to have a plan in place for getting some fresh seafood during the rest of your trip. New England is famous for lobster rolls, clam chowder, oysters, and so much more, and Portland is home to some of the most incredible seafood restaurants in the region!

For a more upscale seafood meal, you’ll want to make a reservation at Scales. Located in Old Port, they have a great raw bar here, and serve up local clams and mussels. Eventide is also an excellent seafood restaurant for a sit-down dinner, and they serve wonderful local oysters.

For the perfect Maine-style lobster roll and great water views, head to Luke’s Lobster at the pier.

6. Visit The Breweries

Not only does Portland have an exciting culinary destination, but its craft brewery scene is equally as great. The city is home to over 60 craft breweries as of 2023, and each one brews amazing beer to try, with a big focus on New England IPAs.

One of the most well-known breweries to check out is Allagash. Known for their ales, and also for having probably the best outdoor beer garden in the city, this is a great one to check out for a fun atmosphere. 

One of the best breweries in Portland, Maine to visit is Bissell Brothers, which is known for its IPAs. One particular double IPA they make that’s more than worth ordering is Swish, which is one of the top-rated beers in the city. 

For more great brewery experiences, also check out Lone Pine, Foundation, and Austin Street. But really, most breweries in Portland are pretty great, so it’s hard to pick a bad one. 

7. Walk The Eastern Promenade Trail

Inside the Eastern Promenade Park, which is a beautiful 73-acre nature area in the city, you’ll want to check out the Eastern Promenade Trail. This paved pedestrian and bike path is just over 2 miles long and allows you to enjoy coastal views the entire way. 

The trail is an easy and relaxing walk, with very little incline, so it’s perfect to do year-round and is especially great with kids. The best place to start is at Fort Allen Park, which is just about a mile from Old Port, allowing you to see parts of this area on your way.

8. Enjoy The Views From The Portland Observatory

As the only surviving marine signal station left in the U.S., the Portland Observatory is a great landmark to visit that offers both history and wonderful views of the city. 

A National Historic Landmark, the Portland Observatory was built in the early 1800s so boats could be seen coming into the harbor, and it was an integral part of the harbor’s efficiency until the 1920s when two-way radio signals were available.

Now, the tower is open seasonally to the public, and guided tours are given of the building, including the top observation floor, which is where you’ll get incredible views of the city and harbor. 

9. Spend The Day On Peaks Island

One of the stops you can make while riding the Casco Bay Island Ferry line is Peaks Island, which is one of the best things to do in Portland, Maine. Peaks Island is just a short 17-minute ferry ride from the city and makes for a wonderful day trip.

Peaks Island spans only about 4 miles, so it’s very easy to explore at a relaxed pace. Once you get off the ferry, you’ll have options to rent a bike or golf cart to explore the island, and both are very fun options! Even though the island is small, it’s best explored with a bike or golf cart, so have a plan in place when you arrive.

For things to do on the island, check out the Umbrella Cover Museum, stroll through the quaint downtown, explore the beaches, grab a famous cinnamon roll from Peaks Café, and take in the views from Picnic Point. 

10. Visit Victoria Mansion

Perfect for those interested in art, history, and architecture, Victoria Mansion is a landmark in Portland to have on your radar. A stunning example of 19th-century architecture, the Mansion is open seasonally for tours. 

Inside, you’ll find opulent period furnishings and a glimpse into what life was like when it was first built in the mid-1800s. It’s said that Victoria Mansion is a one-of-a-kind estate, which makes it special to experience in person. 

11. Find Your Favorite Whoopie Pie

Maine is famous for its whoopie pies, and once you arrive, you’ll see these delicious little treats in bakeries and cafés all over. During your visit, one of the best things to do in Portland is find your favorite whoopie pie, as the city is home to some of the best in the state. 

A fantastic bakery to check out during your visit is Two Fat Cats, which serves up not just a wonderful whoopie pie, but also delicious cookies, brownies, pies, and so much more. They also typically have seasonal whoopie pie flavors on their menu, including lemon zucchini and wild blueberry, pumpkin, and strawberry. 

12. Sip On Creative Cocktails

While Portland is known for its exciting brewery scene, it’s also home to some amazing bars that serve specialty cocktails worth seeking out. If you’re not a beer person, you’ll want to have these places on your radar.

One in particular that’s especially perfect to visit is Batson River, which is a brewery, distillery, and restaurant all in one. With a unique atmosphere that’s definitely Instagram-worthy, and creative drinks on their menu, it’ll be hard to decide what to order once you arrive. 

Blyth & Burrows is also an impressive place for cocktails. Serving small plates, as well as creative drinks that look as good as they taste, you may want to come back here twice during your trip.

13. Enjoy The Portland Museum Of Art

The Portland Museum of Art is the largest and oldest public art institute in Maine and is worthy of being on any art lover’s itinerary. 

The walls are filled with over 18,000 pieces of art, and you’ll find works by Andy Warhol, Monet, Jackson Pollock, and Renoir. 

If you’re traveling on a budget, the museum is free to all visitors on Friday nights from 4-8 p.m. 

14. Ride The Maine Narrow Gauge Railroad

One of the most fun things to do in Portland, Maine is take a ride on the Maine Narrow Gauge Railroad. Hop aboard historic steam and diesel trains, and ride along the coast with views of Casco Bay. 

Each ride on the railroad includes interesting history and narration, and you’ll learn why Maine installed a system of these unique 2-foot wide gauges that were a first in North America. 

For an even more unique experience, you can book a special seasonal ride, which is offered throughout the year. In the summer, ice cream train nights are available, with pumpkin rides in the fall , and a festive Polar Express Christmas train during the holidays. 

15. Experience The Magical Christmas Festivities

New England in general really knows how to celebrate the holiday season, and Portland is no exception! If you happen to visit in December, there are so many wonderful festivities to enjoy that’ll definitely put you in the holiday spirit.

The Portland Parade of Lights is an especially fun one to experience, where you can enjoy watching a parade of boats sail across the harbor, each featuring its own unique display of Christmas lights. 

Portland also has a few Christmas trees to see, and you can typically attend lighting ceremonies the weekend after Thanksgiving. The Old Port tree is one of the best in the city to see, and the lobster trap tree by Luke’s is sure to put a smile on your face. 

Best Time Of Year To Visit Portland, Maine

Portland is truly a wonderful city year-round, but there are definitely some things to know when deciding on the time of year to visit. 

Peak season in Portland is June through September, and this is when hotel prices will be at their highest, and when you’ll experience the most crowds. The trade-off is you get some of the best weather the city will experience, with long warm days, and fewer chances of rain.

Portland, Maine in October  is also a wonderful time to visit, as you’ll start to see hotel prices drop, and the crowds will begin to thin out. You’ll also get to enjoy fall foliage around the city and experience cooler weather. October is typically the last month that boat tour companies will be open, so this is also your last chance to book any sailing or boat tours around Casco Bay.

If you’re visiting on a budget, consider visiting Portland, Maine in November , or the winter months after the holidays are over. Hotel prices in November are even lower than in October, but the weather isn’t quite as cold as the winter season, making this an underrated time to visit.

In the winter season, Portland makes for a cozy getaway that’s filled with great food, museums, and brisk walks along the coast. Portland doesn’t get as much snow as the northern parts of Maine, so it’s still easy to visit this time of the year.

How To Get To Portland, Maine

The closest airport is Portland International Jetport Airport, which is only about 10 minutes outside the city. For more flight options, you can also fly into Boston Logan International Airport, and drive about 2 hours to Portland.

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How To Get Around Portland, Maine

Downtown Portland is easy to navigate without a car, so if you’re planning to only visit the city, a car won’t be necessary. If you’re planning to visit Portland as part of a larger trip around Maine or New England, you’ll want to have a car with you and look for hotels with parking areas on-site. 

Portland has lots of public transportation available to get around, including buses, trains, and ride-share services like Uber and Lyft. But really, most of the city is pretty walkable.

The only time a car will come in handy is when you plan to visit the lighthouses in South Portland. For this, it may be worthwhile to pick up a Zip Car, which is parked all over the city and easy to find. Alternatively, you can book a lighthouse tour so you don’t have to worry about getting a car.

Now that you have the inside scoop on all the best things to do in Portland, Maine, you’re ready to plan the perfect coastal city escape!

With so many fun things to do, the hard part is choosing how to see it all during your trip. Whether you’re hoping to tour all the lighthouses and enjoy a lobster roll (or two!) along the way, or you’re excited to shop in Old Port and sip on craft brews, one thing’s for sure – you’ll have such a memorable trip to Maine after your time in Portland.

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26 Unique Things to Do in Portland, Maine

I popped up to the pine tree state for a few days to attend the Women in Travel Summit, and I was absolutely charmed! Here are all the unique things to do in Portland, Maine if you find yourself visiting. Just a warning, they’re probably 90% food-related.

Surprise! I went up to Maine recently when I said I was hunkering down for the month to get ahead on work. The lovely Alex from  Alex in Wanderland asked me if I wanted to go since she had an extra ticket. I looked up some accommodation options and the logistics of driving up, and thought, “Why not?!” 

It was such a great weekend! I always get anxious thinking about attending conferences, and then I wind up have the best time. It’s not everyday you get to hangout with people who love travel like you do, and, wow, did WITS bring some incredibly inspiring speakers this year! Seriously, just look up Deesha Dyer and Deidre Mathis.

Of course, in between the conference talks and sessions, I wanted to get to know Portland! Between saving some places on my phone, chatting with my hostel roomies, and asking random locals about the city, I wound up doing quite a lot in only a few days. Here’s all I got up to!

Why Visit Portland, Maine

If you’re not familiar with Maine or New England, there’s a certain vibe to the area that’s quite unique. See Taylor Swift’s Red era when she was dating the Kennedy kid or, you know, the Kennedy family and Hyannis Port, but maybe not as WASP-y.

Portland, which is more in southern Maine, embodies all of it and mixes it with what feels like a bit of its own hipster touch. Oh, and, of course, layers it all with an abundance of delicious food and restaurants with their own personality. 

Map of Things to Do in Portland Maine

Tips for Visiting Portland 

Where to Stay

Budget: black elephant hostel.

This is where I stayed! It’s hands down one of the cutest hostels I think I’ve ever stayed at. I mean, just look at that pupper modeling like it’s his day job. (Sadly it seems he’s since passed!)

The hostel isn’t right in the center, but it’s kind of a nice midpoint between the waterfront and Portland Observatory and downtown. I slept in a 6-bed female dorm, and my roommates were awesome! We chatted about where to eat, the conference, and just travel in general. It was a pretty spacious room, and we had our own bathroom plus bathrooms in the hall and a nice sink area.

Book on Booking or Hotels.com

Mid-Range: Holiday Inn by the Bay

This is where we had our conference, so I thought I’d add it as a bit of a mid-range option (still around $200+ a night). It’s very close to everything downtown and across the street from the Portland Museum of Art. 

Luxury: Press Hotel

I feel like if you want a luxury stay and you find an Autograph Collection hotel, stay there! All the hotels are independently owned and operated, so they remain unique, and often the designs fit the vibe of the city they’re in. I stayed at one in Kissimmee , and I’m still so obsessed with the decor there.

The Press Hotel is right in the middle of downtown, and I walked by it frequently visiting other places. Of course, peeking at photos, it’s easy to see how beautifully it’s decorated!

I just switched to AT&T on my recent trip home since T-Mobile was crap abroad and I never seemed to get even semi-decent service stateside. I had plenty of service in Portland and never had an issue connecting to data. 

Wifi was also fine most places I went. It was a little wonky at the Holiday Inn, but I also assume that has to do with the fact that a giant conference of female travelers was going on, and we  all are digitally connected.

You  should be able to pick up a SIM card at the airports, but if you can’t, try to get to an AT&T store, and they can help get you set up. 

What to Pack/Expect for Weather

I can’t believe I forgot this, but Maine is kind of cold! Now that I’ve been back, I remember camping in Bar Harbor and wearing the same long jeans everyday because it was so cold in the summer. Portland in early May is no exception. I was dressed poorly for the entire trip with summery dresses, skirts, and sandals. 

If I was repacking, I’d bring my trench coat and pack some nice slacks and pants with some cute tops instead of dresses. I’d also swap out my sandals for my loafers.

Transportation Logistics

The closest airport to Portland is  Portland International Jetport (PWM)  and it’s only a 10-minute drive to downtown Portland. You can easily grab a Lyft over or rent a car. 

How to Get Around

Portland is pretty walkable if you’re worried about renting a car. And if you walk too far and don’t want to walk back, there are plenty of Lyfts. Bug Lighthouse and Portland Lighthouse are a bit of a drive away, so you’ll probably want to drive to them.

I personally drove since I had my car and I needed to keep moving it. The parking near Black Elephant was only 2 hours between 9am – 5pm but free the rest of the day, so I constantly drove it over to the Holiday Inn, where we had free parking for the conference.

26 Unique Things to Do in Portland Maine

1. Grab a donut at Holy Donut

My friend RAVED about these donuts when I told her I was going to Portland. She said they’re even better than the Duck donuts I dream about from Ocean City, MD. 

Naturally, I went to try one. There are three locations: Park Ave., Exchange Street, and Scarborough, and I went to the Exchange Street one and, later, to the Scarborough one. They’re made from as many local ingredients as possible, and the Maine one is — potatoes! (Get it main, Maine, heh heh). 

They’re freaking delicious, and I didn’t even know about how much healthier and more locally-sourced they are when I got them! My first taste was toasted coconut, and then I picked up a half dozen to bring back to Corinne. I can’t remember which ones I got, but my favorite was maple bacon! 

2. Get a lobster roll at Portland Lobster Co

As soon as I rolled into Portland, I stopped here for a late lunch! It was my first experience of the city, and it was such a nice one at that. The cashier was so lovely, and the lobster roll was amazing. They also serve local Maine Root soda, which made me then ask for it everywhere I went. All their seafood is locally-sourced and as organic as they can make it. Even their straws are biodegradable in case you forget your own.

Highly recommend sitting outside. If it’s cold out, they have a heated tent section.

3. Check out the books at Longfellow Books

Okay, there are quite a few bookstores I saw around Portland, but I saw Longfellow recommended the most, and I loved it. I got two used books, a cute notebook, and the most adorable card with “There She Goes” on it! Can you tell I’m a sucker for bookstores? 

4. Grab a cone at Mount Desert Ice Cream

Before a WITS happy hour, I met up with Alex at Mount Desert Ice Cream (which, lol to ice cream when we’re freezing in the drizzly weather). All their ice cream is totally homemade. I loved the Maine sea salt caramel flavor.

5. Try the Chinese at Empire Chinese Kitchen.

So when I was checking out at Longfellows, I asked the woman at the register if she had any favorite places to eat in Portland. Empire was one of those places, and we wound up there after the conference finished the first day. 

DELICIOUS. There’s usually a bit of a wait for dinner, so I’d reserve ahead if you can. They even have soup dumplings, and the soup-meat ratio was on point. On par with the ones I had at Din Tai Fung in Kuala Lumpur. I also got duck ramen which was also mouth-watering.

6. Get a giant slice of pizza at Slab

Another place she mentioned was Slab pizza! Holy pizza, guys. It’s HUGE. Don’t get more than one slice because you probably won’t even be able to finish it. Also get the root beer with it, yum!

7. Dine at DiMillo’s on the Water

We had happy hour at DiMillo’s and it was a fun place to mingle and chat. The restaurant is on a ship in the marina, and you can grab dinner or lunch there.

8. Grab some fish and chips at Tomaso’s Canteen

We went here after finding out Eventide had an hour wait. It’s a casual bar right near Black Elephant Hostel, and the fish and chips were especially good! 

9. Walk around Old Port.

Of course, the best way to get to know the town is to walk around the Old Port. I did a little walking on my first day. It’s a super walkable city, especially the downtown area since everything is pretty much with in a 1/2 mile radius.

Old Port Tours

• History Tour with a Sweet Treet
• Historical Walking Tour
• Old Port Culinary Walking Tour
• Vintage Fire Truck Sightseeing Tour

10. Sip on some tea and get cozy at Dobra’s Tea Room

I mean, Maine was drizzly and cold in early May, so I can’t imagine how it is in the fall, winter, and early spring! Cue a nice hang out session at Dobra’s Tea Room, probably the coziest places I visited on my trip.

They even have those nice dais beds where you need to take off you shoes to sit and enjoy. Choose from a  ton of teas from around the world. I loved the one I got. I can’t remember the name, but it was third on the menu of flowering teas, and I had it with matcha cheesecake.

11. Eat lunch at Green Elephant

I say lunch because Corinne told me she tried eating there for dinner, and it had a crazy waitlist, so you may have better luck at lunch. This was the third place the Longfellow cashier told me about, and I’d say she was 3/3 on her recommendations!

The Green Elephant will be awesome if you’re with vegans or vegetarians. It started in 2007 to be the ultimate place for vegetarians in Portland, and many of its dishes are Asian-inspired. Definitely get the Pad Thai and then sorbet for dessert! I did try the Mexicane cola here and didn’t love it as much as the root beer from Slab.

12. Get some Italian at Paciarino

Rae and I got dinner here! She said she was craving pasta, so I looked up nearby Italian places and Paciarino was the closest one! They hand make their pasta and sauces everyday, and the ravioli milano was so, so good. Our waiter also recommended our next stop!

13. Eat gelato at the CUTEST gelato place in the USA

If you get gelato anywhere in Portland, get it at Gorgeous Gelato, which is maybe a 5-minute walk from Paciarino. Don’t let the line phase you, there won’t be much of a wait, and the owners were so sweet. We spoke with Mariagrazia as we were paying, and she wound up recommending a gelato shop for me to try in Milan (will update with that one). 

The gelato and canoli we got were, of course, delicious!

14. Go to an event at the Grace

We had our opening party here! It was once a historic church and was redesigned as an event space. While it’s probably more used for things like conferences and weddings, they do have other events, like yoga! Just check their site for anything you might want to go to. 

15. See Portland Observatory

The Portland Observatory was originally built in 1807 and is now the only one of its kind still left. It’s 86ft (26m) high. Basically, because of the way the harbor is, not all ships were easily visible as they were coming in. So, they built this observatory so that people in the wharfs and the ocean could see it. 

I wasn’t in Portland in season, so it was closed, but if you go between late May and mid-October, you can take a guided tour. It’s $10 for adults and will, of course, give you a pretty view of the city!

16. French pastries at BLVL

Stop by BLVL or Belleville after you check out the Portland Observatory for some delicious French pastries. I actually parked next to it without realizing it was a cafe, so I was happy to not have to stop off elsewhere for coffee. Their ice coffee was a bit too strong for me, but I’m also still getting over not putting heaps of creamer and sugar in mine, so if you’re a regular coffee drinker, you might love it. The pastry I got with an egg in the middle, though, was delicious.

17. Check out the Portland Lighthouse

Take the morning and drive out to the Portland Head Lighthouse in Cape Elizabeth! If you want to spend the day outside, you can enjoy the whole Fort Williams Park. The lighthouse was first built in 1791 and is 101ft (31m) high. It’s considered the oldest in the whole state.

The drive is pretty easy and only takes maybe 15-minutes. If you go during the weekend, you can visit the Lighthouse Museum for $2. 

Tours to Portland’s Lighthouses

• Portland City & Lighthouse Tour
• Lighthouse Bike Tour
• Sunset Charter in Vintage Lobster Boat

18. Then pop over to Bug Light and see some harbor views of Portland

On your way back into Portland head to Bug Light Park! Bug Light, which is officially known as the Portland Breakwater Lighthouse, is a cute, tiny lil thing. It was first constructed in 1855 and the current tower is from 1875. It’s tiny compared to just about any other lighthouse I’ve seen at only 30ft (9.1m)! 

And, of course, the park is a great place to see views of the harbor and Portland from afar! Can you see the Portland Observatory peeking out?

19. Enjoy the Eastern Promenade/waterfront

If the weather is nice, go for a walk around the waterfront! It’s just a nice, quiet area with pretty views.

Unique Things to Do in Portland, Maine that I Didn’t Do Yet

20. Check out Portland’s many breweries – I don’t drink beer, so I, of course, am not the target market for this one! However, Portland has a ton of cool breweries. You can check them out on your own, or try a craft drink tour, like this one. There’s also this bikes and brews tour if you want to mix in some sightseeing or this brews cruise if you want to kick back on the water.

21. Go to Duckfat –  I want to try those fries fried in duck fat!

22. Eat at Eventide Oyster Co. –  Everyone  raved about this place, but the only time we were planning on going, it was an hour wait and you can’t call ahead. Next time!

23. Portland Art Walk & Portland Museum of Art – On the first Friday of every month, you can go on an art walk around the town and the PMoA is free! It was too cold and rainy the Friday I was there, so I didn’t want to stay outside too long.

24. Victoria Mansion –  Want to see how the wealthy New Englanders lived in the 19th century? Take a tour of Victoria Mansion! WITS had some tours, but you needed to pre-register and I was too late.

25. Two Lights State Park –  Another lighthouse! I wish I had seen it on the map beforehand, and I would have made to stop by.

26. Island Hopping –  There are so many islands near Portland! I want to try to see more of them if I go back, but I haven’t done much more research beyond jotting down some names. 

For more on Portland:

• Day Trips & Outdoor Adventures Around Portland
• Frommer’s Maine Coast Guide
• Fodor’s Maine, Vermont, and New Hampshire Guide

And there you have it! A fun, little guide on all the unique things to do in Portland, Maine!

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13 comments.

Hi Samantha, You mentioned “Portland Lighthouse” but the correct name is “Portland Headlight” or Portland Head, as some of us natives call it. By the way, poet Henry Wadsworth Longfellow would walk from his Portland home to Portland Head frequently. He was internationally known in his day.

I’m so glad that you mentioned Victoria Mansion, which is the work of a nationally distinguished architect and this is his only surviving work.

For historic cemetery fans, there’s Eastern Cemetery and their Spirits Alive tours are wonderful. And Friends of Evergreen Cemetery offer docent-led tours, which often are theme-based. “Suffragettes” “Sea Captains” “Civil War” I’m glad that you enjoyed visiting my hometown. I cherish that place and its culture. Best wishes and happy travels, Patricia

Being a sucker for bookstores like you makes me want to visit Maine ASAP. I can’t wait to get my hands on those cute little notebooks. The pictures of donuts & ice cream make me drool. Hanging out at Dobra’s is definitely on my bucket list…

It’s SUCH a cute city and really does make for the perfect little trip between sightseeing, food, and local shops!

I thought this post was about travel not food haha :)

Haha travel and food go hand in hand!

Samantha, I have lived in Portland for over 30 years. You did a great job of covering all of our favorite places. I totally agree when you come back you definitely have to have the worlds best French fries at DuckFat. Oh and some people will be excited to hear that because of Covid and many many restaurants moving their dining outside, yes in tents in the winter, Portland has decided to close many of the streets in the Old Port so it will be foot traffic only. 47 restaurants have agreed to go along with inside and outside dining. Similar to Burlington VT. So you and all your readers definitely come back! It’s so exciting your plan to visit the world. You go girl!!!

Hi Susan, thank you for your kind words! Ugh just saying “french fries at DuckFat” has me salivating, I can’t wait to finally try them. That’s so cool about some streets being foot traffic only and how many restaurants agreed to outside dining. And aw thank you! I do love travel ha!

The food looks so good and the places are just so serene…Lovely…Thank you so sharing!!

Of course <3!

I was just looking at blog names and thought yours was perfect; and low and behold the post that came up was this one, where I am from! Great post! Recommendations if you come up again Thai food from Boda, stand up paddle board yoga by Portland Paddle, coffee from a Coffee by Design and an event at Thompson’s Point!

Aw thank you! Haha the song my blog name is from is forever stuck in my head! Definitely noting all of these for a return trip!

My plane just landed back home and you already wrote a kick-butt post about our trip! Love this so much ♥️

Hehe, thank you!

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5 replies to this topic

Any grocery store chains that typically sell rotisserie chicken?

Hannaford's and Shaw's normally have rotisserie chickens

There's a Hannaford's on Forest Avenue, just a slight detour to your hotel. There's a Costco that's less than 15 mins from the Airport. It's south, though. There's a Trader Joe's nearby your hotel as well.

There is a large hannafords off I-295 (Forest Ave) that will have rotisserie chicken.

Perfect! That gives us several convenient options.

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Portland Hotels and Places to Stay

Discover Coastal Charm: Where to Stay in Portland Maine

C hoosing where to stay in Portland, Maine, depends on what you’re planning to do during your stay. If, like me, you’re interested in the city’s great restaurants, check out the hotels in Old Port and do an epic food crawl.

Traveling to Portland on a family vacay? My son and I got a kick out of the “world away” vibe at the Inn at Diamond Cove. Located on a Casco Bay island, it’s reached by ferry or water taxi from downtown Portland.

Couples traveling to Portland looking for a romantic retreat that’s cozy and quiet at the end of a long day might want to stay in Portland’s residential West End.

Here’s our guide to where to stay in Portland, Maine, by neighborhood.

Old Port Hotels

The Old Port neighborhood in Portland is a vibrant and historic district known for its bustling waterfront. With cobblestone streets, charming brick buildings and a world-class restaurant scene, Old Port is considered by many to be one of the best areas of Portland Maine. Explore unique boutiques, art galleries and enjoy fresh off the boat seafood and book a stay at one of the city’s best hotels.

Portland Harbor Hotel

468 Fore St.

Portland, ME 04101

You can’t help but notice the distinctive red brick facade of the Portland Harbor Hotel . Featuring 101 guest rooms in a variety of configurations including deluxe rooms, garden view rooms, junior and executive suites.

The hotel has an on-site restaurant, the Harbor Bistro, with a terrace you can enjoy on warm summer nights. Pets are welcome; a $100 per night fee applies.

Featured amenities of the Portland Harbor Hotel:

• Complimentary wifi
• Fitness center
• Room service
• Event spaces for meetings and weddings
• Outdoor patio with fire pits
• Complimentary coffee and tea in the lobby
• Valet parking – daily fee applies

Cambria Downtown Portland

25 Hancock St.

Portland, ME, 04101 

Want a new hotel while exploring Old Port? The Cambria Downtown Portland opened in 2022 next to Shipyard Brewing, one of the city’s great breweries. It has 102 guest rooms and a unique 4th floor lobby and dining patio for great city views.

As a participating Choice Hotels lifestyle brand, you can earn or use Choice Privileges Rewards points.

Featured amenities at the Cambria Downtown Portland:

• State-of-the-art fitness center
• Design-forward accommodations
• Free wifi in the tech-friendly guest rooms
• Spa-inspired bathrooms

East End Hotels

Also referred to as Munjoy Hill, the East End neighborhood is another of Portland’s residential neighborhoods with an oceanfront promenade for strolling.

Be sure to include a visit to the Portland Observatory. The 86-foot-high former communications tower offers the best views of Portland.

Portland Regency Hotel & Spa

20 Milk St.

This historic boutique hotel seamlessly combines old-world charm with modern amenities. It’s located on the eastern fringe of Old Port, perfect for exploring the East End.

The Portland Regency Hotel & Spa features elegantly designed rooms, a full-service spa and an award-winning restaurant.

Featured amenities at the Portland Regency Hotel & Spa

• 95 luxurious rooms and suites
• Deluxe bedding and plush bathrobes
• Luxurious marble bathrooms
• Full service spa

Arts District Hotels

Portland’s Arts District serves as the city center for artistic expression and creativity. If you stay in the Arts District, you’ll find numerous art galleries, theaters and performance venues including the Portland Museum of Art and the Merrill Auditorium within walking distance. The monthly First Friday Art Walk, sponsored by Creative Portland, draws thousands of visitors to the district.

The Press Hotel

119 Exchange St.

This Marriott Autograph Collection is THE place to earn or use your Bonvoy points. Once the home of Portland’s daily newspaper, The Press Hotel is decorated with vintage typewriters. Even if you’re not staying here, pop in for a look at the hotel’s art gallery.

The design of the 110 guest rooms was inspired by 1920s writers’ offices. They’re crisp, tailored and chic with luxe Frette bed linens. The Press Hotel has two onsite dining options: Union is a full-service restaurant and Inkwell offers morning coffee or evening cocktails.

Featured amenities at The Press Hotel

• 24-hour front desk
• Meeting and event spaces
• In-room spa services available
• Bicycle rentals
• Unique newspaper-themed decor

Holiday Inn by the Bay

88 Spring St.

Portland ME 04101 

IHG One Rewards members can earn or use points at the Holiday Inn by the Bay , a 239-room property in Maine’s Arts District. Choose a room on one of the hotel’s upper floors for sweeping views of Casco Bay.

Note: The Holiday Inn by the Bay is currently undergoing a complete multi-million dollar property modernization. Expect construction between the hours of 9:30 am – 7 pm.

Featured amenities at the Holiday Inn by the Bay

• EV charging stations
• Large indoor pool, sauna and 24/7 fitness center
• On-site Port of Call restaurant serving breakfast, lunch and dinner
• Complimentary electric bikes in summer
• Complimentary shuttle service
• Free wifi, in-room mini fridge, desk and flat screen tv

West End Hotels

The West End is a primarily residential neighborhood with tree-lined streets and beautifully maintained 19th-century Victorian homes. You’ll want to check out the Western Promenade, an 18-acre public park with an oceanfront walking trail. It’s particularly lovely at sunset.

Want to stay in the quiet West End? It’s a good place to look for AirBnb or VRBO rentals. The Westin Portland Harborview straddles Old Port and the West End. Or pick a charming bed and breakfast.

Westin Portland Harborview

157 High S.

Portland ME 04101

Historic elegance meets modern sophistication at the Westin Portland Harborview . This Marriott Bonvoy member property occupies the former home of the Eastland Park Hotel which opened in 1927.

If you’re looking to unwind during your Portland vacay, the Westin has an onsite spa.

Featured amenities at the Westin Portland Harborview

• 289-room Marriott Bonvoy historic hotel
• Adeline Wellness Spa, Westin WORKOUT Fitness Studio, indoor pool
• Top of the East and Congress Squared restaurants
• Westin Heavenly Beds

Blind Tiger Guest House

163 Danforth St.

Portland, ME 04102

The Blind Tiger complex includes two guest houses in Portland’s West End neighborhood for a charming and intimate accommodation option. There are 15 rooms, some with fireplaces, between the two properties. Each is uniquely decorated to resemble your wealthiest friend’s guest room.

In each house, there are cozy public spaces for relaxing too. A complimentary artisanal toast and yogurt bar is available for guests in the morning and there’s a pantry with locally sourced snacks and beverages open throughout the day.

Featured amenities at the Blind Tiger Guest House

• Limited off-street parking
• Free high-speed wifi
• Picnic blankets and baskets to borrow
• Bath amenities from Lather and waffle kimono robes

South Portland Hotels

Don’t overlook South Portland when considering where to stay. You’ll lose the walkability downtown Portland offers. But that’s offset by other attractions. Explore Willard Beach, a picturesque sandy beach known for its stunning views of the Atlantic. History buffs can explore the Maine Military Museum with its impressive collection of artifacts and exhibits detailing the state’s military history. And shopaholics can indulge in retail therapy at The Maine Mall , the second-largest shopping center in New England.

And, best of all, your stay in South Portland will cost much less than a stay downtown. Nightly rates at the hotels in Old Port continue to climb as the city’s popularity as a destination grows. Last year while planning a birthday trip with my girlfriends, we were floored by mid-week prices at $500 per night for downtown hotels!

Clustered between the PDX Portland International Airport and The Maine Mall you’ll find many of America’s most well-known chain hotels with expected amenities, including:

• Fairfield Inn
• Hampton Inn
• Home2Suites by Hilton
• Courtyard by Marriott
• Embassy Suites
• Hilton Garden Inn

Because they’re proximate to the airport, many of these chain hotels offer a complimentary airport shuttle, if you’re arriving by plane.

Places to Stay Near Portland, Maine

There are a number of great places to stay near Portland, Maine where you’re still close to the city’s restaurants, shops and attractions. They’re appealing for many reasons. Some are budget-friendly while others are in great natural settings to add another dimension to your vacation.

Inn at Diamond Cove

22 McKinley Court

Portland, ME 04109

This hotel has a Portland address, but it’s a world away from the hustle and bustle of the city. And it’s one of my favorite places to stay while visiting Portland, Maine. Just getting there is an adventure. You’ll need to book a water taxi or hop on one of the Casco Bay ferries. The hotel occupies a campus of restored brick military buildings.

The rooms are huge and comfy. The outdoor pool is ideal for a dip on a warm summer day. And the island is fun to explore on foot or by bike. Plus there’s an amazing destination restaurant – Diamond’s Edge – at the marina. Mainlanders ferry over for dinner. It’s that good. All of the details can be found in my Inn at Diamond Cove review .

Featured amenities of the Inn at Diamond Cove

• 44 deluxe guest rooms and suites
• Outdoor pool with snack bar
• Rec building with basketball courts, duckpin bowling, ping pong

Inn by the Sea

40 Bowery Beach Road

Cape Elizabeth ME 04107

Although you’re minutes from downtown Portland, you’ll feel a world away at the Inn by the Sea in Cape Elizabeth, home to the iconic 18th-century Portland Head Lighthouse.

This luxury beachfront resort is family- and pet-friendly. If you want a truly special summer experience at the Inn by the Sea, make reservations for one of the seven scheduled clambakes. You’ll have all the fun with none of the mess!

Featured amenities at the Inn by the Sea

• 62 guest rooms and one- and two-bedroom suites
• Miles of sandy Atlantic beach
• On-site full-service spa
• Destination dining at the inn’s Sea Glass restaurant

Spacious Skies Walnut Grove Campground

599 Gore Road

Alfred ME 04002

If your Maine adventure includes Portland and other Southern Maine destinations like Kennebunkport and Old Orchard Beach, you might want to stay outside of the city. The Spacious Skies Walnut Grove Campground has RV sites, cabin and retro camper rentals, plus a ton of campsite amenities about 40 minutes from downtown.

• 93 RV sites, 3 cabins, 2 retro campers
• Heated outdoor pool
• Playground, jumping pillow and gem mining for the kids

Because Portland is a small, walkable city, you can’t go wrong no matter where you choose to stay. It’s an iconic Maine destination as a standalone weekend getaway or part of a longer New England road trip. The vibrant port city retains its historic charm with cobblestone streets and gorgeous Victorian homes and many fun things to do .

It’s no dusty relic. Portland’s one of the top culinary destinations in the US where even the dive bars serve meals you’ll remember for years to come. And there’s a thriving arts scene with galleries, studios, performance venues and a very popular First Friday Arts Walk.

The post Discover Coastal Charm: Where to Stay in Portland Maine appeared first on She Buys Travel .

‘It’s torn our community apart’: Rift deepens over Portland Museum of Art expansion plan

Is the multimillion-dollar ‘landmark for the future’ at odds with protecting portland’s historic downtown that’s the question at the heart of a contentious debate in maine’s largest city..

P ORTLAND, Maine — In order for the Portland Museum of Art to thrive into the future, Mark Bessire believes it needs to dramatically change.

“Our buildings are dedicated to viewing art in a more traditional sense,” says Bessire, the museum’s director. “And traditional museums are, to a certain extent, elitist. We don’t want that feeling, we don’t want that look. We’ve changed.”

But a grandiose expansion plan that would radically remake the museum is sparking a fierce debate as decision-makers in Maine’s largest city weigh the museum’s desire to build a multimillion-dollar “landmark for the future” with the need to protect another of Portland’s prized cultural assets — its historic downtown. Critics of the proposed makeover, including Bessire’s predecessor, accuse the museum of waging a cynical PR campaign to justify the enormous new building.

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“I’ve been really saddened to see the way it’s torn our community apart,” City Councilor Kate Sykes said at a meeting last month.

Over the objections of both the Planning Board and Historic Preservation Board, Sykes and her colleagues have, for now, sided with the museum, giving it a green light to tear down a building that is — or was — part of a federally recognized historic district and replace it with an ultramodern 60,000-square-foot addition that will double the size of the museum.

But the proposed expansion, a four-story, glass-and-timber structure expected to cost upward of $100 million to build and operate, is hardly a done deal. Preservationists are exploring legal options to prevent the museum from proceeding with its plan to bulldoze the stately, columned structure next door, and city officials have yet to scrutinize and approve the design details of the massive addition.

“There’s a lot of stuff in the plan that is problematic,” said Alex Jaegerman, Portland’s former planning director and now a trustee of Greater Portland Landmarks, a preservation group that wants to save the abutting building.

The ambitious project comes at a complicated time for the museum, whose attendance, like that of many other cultural institutions, has not rebounded to pre-pandemic levels. Last year, 115,411 people visited the Portland Museum of Art — about a 35 percent decline from 2019, when 176,699 visitors walked through the door. In February, citing financial pressures, the museum laid off 13 employees, or about 10 percent of its staff. At the same time, the museum has announced a lofty capital campaign to raise the money for the new building.

“You can’t pick or choose your moment to do the work you need to do,” said Bessire, conceding that the optics of layoffs amid such a large-scale development are not good. “If we wait too long, we could fall so far behind that we can’t actually get to the future.”

Founded in 1882, the Portland Museum of Art today consists of four buildings that range in age from very old to old. The compound, a five-minute walk from the Old Port, includes the McLellan House, built in 1801; the Clapp House, built in 1832; the Sweat Memorial Galleries, built in 1911, and the striking Charles Shipman Payson Building, a four-story redbrick structure — designed by Henry Cobb , a partner in I.M. Pei ’s architecture firm — that opened in 1983 and spurred something of a renaissance in Portland by attracting tourists and inducing investment in downtown.

But the bloom is off the rose, according to Bessire, who says the PMA lacks not only storage and gallery space for its ever-growing collection, but also “21st-century amenities,” such as a performance hall, classrooms, free space for children and families to roam, a restaurant, and rooftop terrace, which could help draw larger, more diverse crowds. The museum, whose new motto is “ Art for all ,” predicts the addition will enable it to nearly double attendance by 2027 and bring energy to a moribund section of downtown Portland.

“We’re thinking about the folks who go to museums, but also the folks who don’t go to museums,” Bessire said. “I love art dearly, but if museums don’t wake up, we’re going to lose the next generation of visitors.”

At a series of public forums to discuss what the expansion should look like, Bessire said several people mentioned the facade of the postmodern-style Payson Building, calling it ominous and off-putting. As a result, the proposed addition, designed by Portland, Ore.-based LEVER Architecture and chosen from among 100-plus concepts submitted by firms around the world, emphasizes transparency and light. (Detractors dismiss it as a “glass box.”)

“To be honest, the Payson Building is not the most welcoming,” Bessire says. “It’s an intimidating building because you can’t see inside. It’s kind of like a fortress on the outside.”

The museum has been contemplating an expansion for several years and, in 2019, purchased an adjacent property that used to be the Children’s Museum. Preservationists didn’t pay much attention, figuring the building’s pedigree — it was built in 1830 and renovated a century later by the celebrated architect John Calvin Stevens — would protect it from the wrecking ball.

Not so, it turns out. Although the building was long ago designated a “contributing” structure to the downtown historic district and thus could not be demolished, the museum persuaded the City Council in May to reclassify it as “non contributing,” clearing the way for its demolition.

In its application to the city, the museum claimed that changes to the front of the building — it opened as a theater before becoming a Baptist church, the Chamber of Commerce, and, finally, the Children’s Museum — had diminished its historical significance. But it was another assertion that angered some here: The museum argued that the building should be razed because it was “erected during the Jim Crow era” and the white columns of its Colonial Revival style “carry unfortunate legacies of the past into the future.”

In other words, said David Chase, an architectural historian and former curator of the National Building Museum , the structure is a brick-and-mortar embodiment of racism.

“Ridiculous,” scoffs Chase, who lives in York. “I’d guess that at least half the buildings in the Congress Street historic district were built during the Jim Crow era.”

Maine State Historian Earle Shettleworth, who’s been a member of the museum for more than 60 years, agrees. He believes the museum invented a phony argument to get what it wanted. “That’s just foolishness,” says Shettleworth, who resigned as trustee emeritus to protest the demolition plan. “The museum has debased itself in its campaign to denigrate this building.”

But Chris Newell, an educator and enrolled member of the Passamaquoddy Tribe of Indian Township in northern Maine, believes opponents of the museum’s plan are being selective in the history they are preserving. Newell, who consulted with LEVER on the proposed addition, credits the museum for thinking more broadly about the past and the future.

He cites LEVER’s inclusion of a distinctive curved roof line that will cradle the morning sun on the summer solstice — a design feature intended to pay homage to the Native Americans who lived on the Portland peninsula thousands of years before the Revolutionary War.

“Museums are a colonial artifact. Preserving history and art in museums is something that comes with colonization,” said Newell. “Rather than pay attention to just the last 204 years — the length of time Maine has been in existence — why not add the 12,000 years of existence on that landscape of the Wabanaki peoples?”

Among the most vocal critics of the museum’s plan is Daniel O’Leary, who was its director from 1993 to 2007. O’Leary believes there are better sites for the expansion, including a parcel of land behind the Payson Building that the museum bought two decades ago and turned into a parking lot.

But O’Leary is also dubious of the claim that by creating amenities like a rooftop terrace, performance hall, and play spaces for children, the museum will be able to double attendance. And if it doesn’t, he questions whether the museum will be able to afford to staff and operate such an enormous building.

“If the goal is to expand the ability of the museum to present fine exhibitions, very little of the proposed new space serves that purpose,” said O’Leary. “It’s all for show.”

On a recent weekday, most of the patrons strolling through the Portland Museum of Art were visiting from out of town and hadn’t heard the inflated rhetoric for and against the demolition and expansion. But Carl Richter and Patricia Hatfield, an elderly couple from Brunswick, said they have paid close attention to the debate and worry that a sparkling new structure will spoil a downtown beloved for its old buildings.

“I don’t care for the new design at all,” said Hatfield, a retired financial planner. “In fact, I’m appalled. Portland’s tourism relies on its history. They can’t lose that.”

Mark Shanahan can be reached at [email protected] . Follow him @MarkAShanahan .

Bangor Daily News

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Downtown Bangor gift shop likely to close in July

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A Bangor gift shop open since the mid-1980s will likely close in July if its owners, who are preparing for retirement, cannot find someone to take over the business.

The owners of Rebecca’s, Rick and Rebecca Vigue, announced  in January they will retire and sell the business. They said they hope to retire in or around June, but because the Vigues haven’t found a buyer, the store is likely to remain open a little longer to clear out remaining products.

The Vigues, who opened Rebecca’s in November 1985, put the business up for sale with the hope that the next person to acquire it will carry on its legacy as a cornerstone in downtown Bangor. While some have inquired about buying the business, they could not make the financial commitment, Rick Vigue said.

“I think it’s a little difficult for people getting money these days,” he said Wednesday. “The banks are not terribly generous.”

The retail shop, at 43-45 Main St., offers Maine-made products, including chocolates, candles, wine, baby clothing and a variety of antiques. Rebecca’s is also a year-round Christmas shop because when it was launching, the Vigues were looking for a theme to attract customers, and they were inspired by a store they frequented in Portland.

The shop is also known for its Brewer-made ceramic blueberry dishware, which it has sold since its first day in business and still has on its shelves. The hand-painted items are popular not only among local shoppers but out-of-state tourists who visit each year.

The Vigues sold the buildings at 43-45 and 49 Main St. in preparation for their retirement, but the new owners are not interested in taking over the business, Vigue said.

They have not set a closing date, but most merchandise in the shop is 35 percent off, and only a handful of products are being restocked. Display cases, shelves and other fixtures are also for sale.

In February, the Vigues reflected on nearly 40 years  in business and how they will miss their dedicated clientele. Customers near and far have sent the couple well wishes over the past several months, Vigue said.

“We’d love to see the tradition continue and so would a lot of other people, but it’s kind of sad,” he said about the shop’s likely closing. “I’m afraid there is going to be a void on Main Street.”

More articles from the BDN

Full Day of Family Fun in Greater Portland, Maine

24 hour family-friendly vacation itinerary, things to do in this spring and summer in greater portland with kids.

Get everyone together for a family trip to Vacationland. Our vibrant region offers something for every age—from curious toddlers to energetic teens. Dive into interactive museums, scenic parks, and historic landmarks, all designed to create core memories. Test out this 24 hour itinerary for a full day of family fun across Greater Portland.

Photo Credits (clockwise from top): Chris Lawrence, Rocky Bottom Tours, CFW Photography, Children’s Museum and Theatre of Maine

Early Start + Breakfast in Portland

Arrive in the region easily by car, bus, train, or plane. Portland is centrally-located just 2 hours from Boston and 4 from New York. Our Portland International Jetport serves-up direct flights to most major cities. Starting in 2024, The jetport added four nonstop destinations from Portland last year, including year-round service to Charleston, SC and Tampa, FL, and seasonal summer service to Norfolk, VA and Pittsburgh, PA. 

Once you’ve settled into your accommodations , start your day with the fam over a hearty breakfast at one of Greater Portland’s local diners or breakfast hot spots. Early morning dining with kid-friendly faves and inclusive menu items are around every corner. 

Find a cozy spot on the water at Porthole, home to Portland’s largest waterfront deck, and find a welcoming atmosphere for all ages, setting the stage for a day filled with fun and exploration.

Porthole Restaurant & Pub

Try Becky’s Diner on the waterfront for diner classics and locals favorites. Dine alongside the fishers and lobsterers for a delicious and casual meal. 

Becky's Diner

Or how about a stop for a maine potato donut at the renowned Holy Donut. Multiple locations and vibrant atmospheres serving-up iced coffee and savory donuts – like bacon cheddar – for the adults and have a treasure trove of sweat treats for your kiddos to enjoy. Find limited-edition flavors celebrating the best each season has to offer.

The Holy Donut- Commercial St

Stopover at Eighty 8 donut cafe for hot and fresh mini donuts. The whole family will love taste-testing festive hand-dipped and specialty bites like the Bamm Bamm (fruity pebble topped) or Cookies N Cream. 

The Eighty8 Donut Café

Most cafes and donut shops also serve-up local-roasted coffee for those in your party who are looking to get their caffeine fix. 

Morning Activities for Young Kids + Teens

Located in the burgeoning Thompson’s Point neighborhood, Children’s Museum & Theatre of Maine is perfect for young imaginations, packed with interactive exhibits designed to educate and entertain. You’ll find an indoor and outdoor playground for any little ones looking to get some energy out. 

Children's Museum & Theatre of Maine

Check-out marine ecosystems, an observation beehive, a makerspace workshop, and infinite more impressive exhibits scattered across floors of fun. There’s also year-round programming at their very own Maddy’s Theatre.

In the Middle of Downtown Portland you can tuck inside to your own personal plant haven. At Terrarium you can explore the wonders of nature and science with your family. Uncover rare plants. Interact with hands-on terrarium-building, offering fun and learning for older kids and teens interested in building their own ecosystem and watching it thrive.

Another activity for young adults, teens, and tweens coming to the Pine Tree State is X-Golf in Portland. They will be love checking-out the only virtual golf simulator in Portland, Maine. Immersive, interactive screens allow you to learn and improve on your technique. All ages and all ability levels are welcome with guided lessons by PGA pros offering to take your experience up a notch. And for those who may not want to take any swings, there’s a board games, darts, and more to keep your family busy.

X-Golf Portland

Lunch + afternoon adventure.

When lunchtime rolls around in Greater Portland, Maine, it’s the perfect opportunity to immerse your family in the region’s vibrant and welcoming atmosphere. With a plethora of family-friendly dining options, you’ll find a little something for everyone, from cozy cafes to bustling waterfront eateries.

Or stroll through the charming cobblestone streets on the hunt for a mid-day treat. Discover quaint shops selling gelato, whoopie pies, and local chocolates. Restaurants boast colorful outdoor seating, where families can gather to enjoy delicious meals amidst the lively ambiance.

Located in the Old Port by Bell Buoy Park, Flatbread Pizza provides the ultimate family-friendly environment. This spot offers delicious pizzas with organic and locally sourced ingredients. Your kids – and yourself – will want to try our their iconic Maine root beer floats while you’re there.

Flatbread Company

Outdoor exploration with the whole family.

In Portland, Maine, families have an abundance of kid-friendly outdoor activities to enjoy. Embark on a thrilling whale watch excursion, where kids can marvel at the sight of majestic whales, seals, porpoises breaching the surface of Casco Bay. Take a guided tour of our landmark lighthouses. Explore iconic lighthouses like Portland Head Light, one of the most photographed in the country. This landmark offers breathtaking views of the rugged coastline and a glimpse into maritime history – as well as a large amount of greenspace in Fort Williams Park for younger kids to run and play. Older kids can fly a kite or explore the grounds.

For a unique experience, hop aboard the Narrow Gauge Railroad downtown, winding its way through the scenic Eastern Promenade. The train provides a memorable 40 minute adventure for the whole family. During the holidays the train transforms into an annual Polar Express celebration.

Maine Narrow Gauge Railroad Company + Museum

Experience the authentic slice of life of a Maine lobsterman with a hands-on tour that immerses you in the tradition of lobstering. Take the whole crew along to find out firsthand the techniques and tools used to catch these coveted crustaceans. All while gaining insight into the vital role lobstering plays in Maine’s coastal communities. This interactive experience offers a unique opportunity to connect with the sea and appreciate the time-honored practices of Maine’s maritime heritage.

Lucky Catch Cruises

Rocky bottom tours.

Whether spotting whales, exploring lighthouses, or riding the rails, Portland’s outdoor adventures promise excitement and wonder for children of all ages.

kid-friendly dinners options in maine

When it comes to dinner in Greater Portland, Maine, families are spoiled for choice with a plethora of kid-friendly options at casual restaurants scattered throughout the city. From cozy bistros to bustling eateries, there’s something to satisfy even the pickiest of eaters.

Bayside Bowl is where family-friendly dining meets entertainment. This multifaceted venue boasts a rooftop bar with stunning views of the city skyline and a taco truck serving up burritos, quesadillas, shrimp tacos, and more. While parents enjoy artisanal cocktails and 3 for $12 tacos, older kids can catch a movie or show on the rooftop. Younger kids will love getting in a round of bowling before the night is out as well.

Bayside Bowl

For those seeking a unique dining experience with a side of excitement, look no further than Junction Bowl. This dynamic venue in Gorham (just 20 minutes from Portland) combines virtual gaming, bowling, and delicious cuisine under one roof, ensuring there’s never a dull moment. If you have teens, you may even be able to sneak away to the Sidecar Whiskey bar next door.

Junction Bowl

Sidecar pub, family-friendly evening fun.

Embrace your creative side at Muse Paintbar, where the whole family can participate in guided paint nights. From personalized pet portraits to kid-friendly themes, these sessions offer a chance for artistic expression and bonding in a relaxed setting.

Muse Paintbar

From thrilling monster truck rallies to interactive dino exhibits and the excitement of a live taping of The Price Is Right, there’s something to captivate every member of the family at Cross Insurance Arena. With its lively atmosphere and engaging performances, the arena promises an unforgettable evening of fun and excitement for families exploring Portland’s vibrant entertainment scene.

Cross Insurance Arena

Extend your trip + start planning.

There is way too much ground to cover to stay for a single night, so make sure to carve out time to explore more of what Maine has to offer. That could mean exploring our area beaches, lighthouses, and charming area towns. Take a trip up to the Coastal Maine Botanical Gardens (under an hour from Portland) to see the Giant Trolls. The gardens offer beautifully landscaped areas and interactive exhibits for the whole family.

Coastal Maine Botanical Gardens

Old Orchard Beach (20 minutes from Portland) features sandy shores, a lively pier, and an amusement park. Stay at the oceanfront Alouette Resort for a front row seat to the excitement.

Alouette Beach Resort

Whether you’re exploring the coastline or enjoying a beach day, Greater Portland offers countless opportunities for families to create cherished memories. Plan your visit today and discover why this vibrant region is perfect for your next family getaway. Plan your trip today.

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Now that the city has ruled on the former children’s museum, what happens next?

What we know about the Portland Museum of Art's expansion plans, a potential lawsuit from Greater Portland Landmarks and the certification of the Congress Street Historic District.

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The latest architectural rendering of the Portland Museum of Art campus expansion as seen from Congress Square and Free Street. Image courtesy of LEVER Architecture

Last month, the Portland Museum of Art got the change it will need to eventually tear down the building at 142 Free St.

Despite opposition, the Portland City Council voted to remove a historic classification that protected the former Children’s Museum and Theatre of Maine from demolition. The museum plans to build a sweeping glass-and-timber expansion on that site as part of a $100 million capital campaign.

Here’s what we know about the future of the site.

What will happen next to the building at 142 Free St.? 

For now, not much.

Graeme Kennedy, a spokesman for the Portland Museum of Art, said the museum continues to work on the design of its new wing with Lever Architecture, based in Portland, Oregon, and Los Angeles. Advertisement

“This includes incorporating feedback we’ve solicited from throughout Maine, specifically working with communities that have not traditionally been welcomed or felt comfortable in a museum setting,” Kennedy said. “Our goal for phase one of this project remains the same – create flexible and open space for art and people to come together in meaningful ways, and we’re looking forward to moving forward.”

Portland Museum of Art hangs its future on fate of neighboring building

The museum is still fundraising for the $100 million capital campaign that will finance the campus expansion. Leaders said $40 million has been raised so far, mostly in endowment. Initial estimates were that construction alone would cost $45 million, although that number has not been finalized.

What is the timeline for demolition and construction?

Kennedy said demolition of 142 Free St. is “not imminent.”

“I don’t anticipate any changes to the site until we have a final concept and building permits have been pulled,” he said.

Kennedy said the museum must complete “a lengthy permitting process” before construction can begin. Advertisement

That process starts with submitting a major site plan application to the Planning and Urban Development Department at the city. The Portland Planning Board would hold a workshop and then a public hearing before taking a vote on the project. Then, the museum would apply for a building permit in order to start construction; a demolition permit would also be needed to take down the current building.

“We are assessing our timelines now that the city has made its decision, and we look forward to sharing updates with our communities in the coming months,” he said.

Last year, the museum said the expansion would not be complete until at least 2026, although Kennedy said that timeline is likely not accurate.

The latest architectural rendering of the Portland Museum of Art campus expansion as seen from High Street. Image courtesy of LEVER Architecture

Is Greater Portland Landmarks going to sue the city over this decision?

We still don’t know.

Carol De Tine, board vice president of Greater Portland Landmarks, said the preservation group has been working with lawyers to determine whether they will challenge the Portland City Council’s decision in Cumberland County Superior Court. She declined to discuss exactly what factors they are weighing as part of their decision. The deadline to take legal action in Cumberland County is 30 days after the May 20 council vote, which would be June 19. Advertisement

“We’re still considering our options, but I have to say that we have heard from a great number of people,” she said. “They’ve called, they’ve emailed to express their outrage and to offer help depending on what we decide to do as we go forward. We’re not done. We don’t by any means think we’re done. No property owner has ever acted with such arrogance and hubris with respect to the historic preservation ordinance.”

Opponents suggest they won’t back down if Portland City Council supports museum’s demolition plan

The building at 142 Free St. is considered a “contributing” structure to the surrounding Congress Street Historic District. Built in 1830 and later renovated by John Calvin Stevens, it has been home to a theater, a church, the Chamber of Commerce and the Children’s Museum and Theatre of Maine.

The Portland Museum of Art asked the city to change the building status to “noncontributing,” which will allow it to be razed. The museum argued that renovations to the building, such as the addition of a dormer and cupola, had altered its integrity under the historic preservation ordinance. The City Council ultimately agreed, finding that the building lacks integrity of design, materials and workmanship.

De Tine said that finding is misguided.

“If someone who lived in Portland in the ’30s walked along Free Street and saw that building, they would recognize it, and that means it really hasn’t significantly changed,” De Tine said.

What about the city’s redesign of Congress Square? When is that going to be finished? Advertisement

Portland is working on a $7.2 million redesign of Congress Square that was supposed to be completed in 2024 but has been plagued by months of delays. The first of two phases is still not complete, and the city parted ways last year with the contractor hired for the project. The city said in March that it now hopes to complete all of the work before the end of summer 2025.

Portland cuts ties with contractor on Congress Square redesign

The first phase, budgeted at $2.6 million, included improvements to traffic flow and sidewalks at the intersection at High and Congress streets, work that was originally expected to be largely completed by fall 2022, with final paving and landscaping to occur the next spring. While Gordon Contracting completed most of the work, a few finishing touches remain, the city said.

Phase two calls for upgrades to Congress Square Park, including the installation of new artwork and improvements to the plaza outside the Portland Museum of Art.

City spokeswoman Jessica Grondin said last week that the city is aiming to get a request for proposals out this spring or early summer in order to hire a new contractor.

Will the Portland City Council’s decision impact the Congress Street Historic District and the possible development of affordable apartments at the Time & Temperature Building?

Chris Rhoades, one of the owners of the iconic Time & Temperature Building in downtown Portland, has said that the change for 142 Free St. could jeopardize the historic tax credits needed to build as many as 250 affordable apartments in the vacant high-rise. The museum disputes the claim that allowing the building’s demolition would affect the federal certification of the Congress Street Historic District, which enables buildings within it to receive tax credits for their rehabilitation. Advertisement

Officials have declined to provided a definitive answer, even after the vote. Grondin said last week that city staff “will proceed with the recertification” with the state and the National Park Service once the 30-day appeal window lapses.

Rhoades said Wednesday that the council’s decision was “a surprising outcome.” He did not have new information about the impact on the Congress Street Historic District and is waiting to see what will happen next. He and consultant Scott Hanson, who previously worked in the city planning department and is advising the project team on historic tax credits, are still concerned that the district will not be recertified.

If the tax credits are not available, Rhoades said, “the affordable housing project goes away.”

Hanson believes Greater Portland Landmarks has a strong case if it files an appeal.

“The council’s decision was based on a fundamental misunderstanding of what ‘integrity’ means in the historic preservation ordinance,” he said.

What will the Portland Museum of Art and Greater Portland Landmarks do to address the public rift created by this dispute? Advertisement

During last week’s meeting, Councilor Kate Sykes acknowledged the fierce debate that has occurred over months. Hearings on the application attracted hours of public comments and dozens of letters on both sides of the issue.

“This is one of the most difficult decisions that I’ve made yet here on the council,” Sykes said. “I’ve been really saddened to see the way that it’s torn our community apart. … No matter how we vote today, there will be disappointed and sad people on the other side of this vote, and we have to go forward as a community and work together after this.”

An architectural rendering of the maker spaces inside the proposed new wing of the Portland Museum of Art on the site of 142 Free St. Image courtesy of LEVER Architecture

But that process of reconciliation will be a difficult one.

“We’ve been saying from the start that we didn’t go looking for this fight, and we feel that it never should have happened,” De Tine said. “The museum should not have put the design before the process of determining whether the building could be reclassified. That’s why it ended up such a difficult issue for all of us. While we’re considering whether we appeal or what we do, it’s hard to think about repair.”

De Tine said Greater Portland Landmarks met with museum leaders twice since last year to suggest other ideas for the site.

“They are just intransigent about continuing with the design that they have,” she said. “It’s a little frustrating for councilors to tell us that we should have compromised, we should have mediated. It takes two to do that, and the museum was not willing.” Advertisement

After the vote, museum Director Mark Bessire posted an open letter to the community on the website for the PMA Blueprint . He thanked everyone who participated in “the vibrant discussions surrounding the proposed new wing.”

“We acknowledge the importance of sharing and preserving the rich history of our properties while simultaneously embracing progress and innovation,” he wrote. “142 Free Street stands as a catalyst for a brighter future, ensuring that Congress Square remains a sustainable hub for arts and culture. The Blueprint project represents not just a physical expansion, but a symbolic commitment to the revitalization of our beloved city of Portland, Maine. We envision a future in which the old and the new coexist harmoniously, in alignment with Portland’s Plan 2030. By developing 142 Free Street, we aim to reinvigorate the arts district, stimulate economic growth and enrich the cultural tapestry of our city.”

Kennedy said in an email that the museum welcomes everyone in the community to participate in the project as it moves forward.

“Our hope is that we can help to create an environment where everyone can feel confident that their ideas are heard and considered. No matter how you feel about 142 Free St., we all want what’s best for the city and for our community. While we may disagree on this particular issue, there are many more areas where we are aligned.”

Related Headlines

Opponents suggest they won’t back down if Portland City Council supports museum’s demolition plan

Portland City Council clears the way for demolition of former children’s museum

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