best little towns to visit in connecticut

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15 Best Small Towns to Visit in Connecticut

Connecticut is the southernmost state in New England, and very close to big-city destinations like New York City. Home to Yale University, this state manages to preserve some beautiful colonial history in its small, rural towns. Get in the car and head out on the back roads to discover what Connecticut has to offer – the scenery along the way will impress you with the beautiful mountains and hills, and foliage.

We’re excited for you to discover this New England small-town charm in our list of the 15 best small towns in Connecticut!

1. Chaplin, Connecticut

Chaplin is located in Windham County, and is named after one of its first settlers, Deacon Benjamin Chaplin. Their main street, Chaplin Street, is a designated Historic Place on the National Register of Historic Places. Come visit this quaint town to curl up in their picturesque library, or to hit the trails around town on foot or horseback!

While you are here, stretch your legs and trek out to Diana’s Pool, a gorgeous nature spot that you’ll fall in love with. Or, if you’re more in the mood for comfort food, try Bach Dor Cafe, a perfect pit stop to indulge your love of fried food. Relax at Passport Inn & Suites and let Chaplin take you back to a simpler time.

2. Colebrook, Connecticut

Located in Litchfield County, Colebrook gets its name from Colebrook County, England. A true small New England town, it is ideal to get away from the stress of everyday life and get back to the basics. Wander the picturesque town, chat with the locals, and stop in at Rock Hall, a Historic Place on the National Register.

This town is at its best during the 4th of July festivities, so be sure not to miss out! You can check out the Colebrook Store for some delicious food that some call “edible history”. Treat yourself to a weekend away at Rock Hall Luxe Lodging and enjoy some time to yourself.

3. Columbia, Connecticut

A town located in Tolland County, Columbia is named after the American ballad Hail, Columbia. Its Columbia Greene Historic District was listed on the National Register of Historic Places, and is well worth your time to explore. The old stone buildings date from the early 19th century and are surrounding a beautiful green that will whisk you away to centuries past.

A perfect stop off the highway, Columbia is bordered by gorgeous nature walks and trees for miles. The town also boasts an excellent train museum. We recommend stopping in during the summer, because the town offers passes to non-residents for summer activities – grab a kayak and have some fun! Indulge yourself with something sweet at Motta’s Pastry & Bake Shop Inc. before continuing on your way.

4. Cornwall, Connecticut

Cornwall is located in Litchfield County, and is a quaint destination sure to enchant you. The poet, Mark Van Doren, wrote a poem about the “Hills of Little Cornwall”, describing the idyllic natural beauty that could be found in the countryside surrounding the town. We recommend a visit especially in autumn to see the colors in all their glory!

Whether or not you’re adventurous enough to strike out into the countryside outside Cornwall, the town itself is also well worth your time. Walk out to the West Cornwall Bridge, one of the few covered bridges in the area. Its red wood is a stark contrast to the greenery surrounding it, so don’t forget your camera. Or, wander town to appreciate the cute buildings reminiscent of gingerbread houses. Enjoy a cup of coffee at Wandering Moose Cafe and stop in at Berkshire Country Store before leaving.

5. Cromwell, Connecticut

Cromwell is located in Middlesex County, near the center of Connecticut. It was named after a boat that sailed along the Connecticut River that was named after Oliver Cromwell. This historic New England town has two separate historic districts, Main Street Historic District and Middletown Upper Houses Historic District, as well as the Sage-Kirby House. Come visit to get a feel for authentic New England old-time towns.

Bring your walking shoes and hit River Highlands State Park. You’ll love the greenery and peaceful view of the river. Or, head out to Cromwell Meadows Wildlife Management Area and explore! Bring your camera and check out the multitude of birds if you’re a bird-watching enthusiast! Take some time to enjoy a meal at Ambrosia and relax.

6. Essex, Connecticut

Located in Middlesex County, Essex is a historic town – it as one of the few American towns to be attacked by a foreign country. During the War of 1812, British vessels arrived and commandeered the town. No casualties were incurred but there were some expensive damages thanks to British looting. Essex survived this and came back strong – it is so beautiful that it was one of the main inspirations for “Stars Hollow” in Gilmore Girls!

Come visit Essex to see a still-running steam train, or stay at one of the oldest inns still in existence, the Griswold Inn. Visit the Essex Library Association to catch up on reading or treat yourself to a day at the Spa of Essex. Have a drink at the Black Seal or enjoy a meal at Olive Oyl’s. Enjoy the taste of history here in Essex, it won’t disappoint you!

7. Kent, Connecticut

Kent is located in Litchfield County, and was founded in 1737. Part of iron production initially, Kent is traversed by the Housatonic River; the town is also home to a historic covered bridge, Bulls Bridge. There is also the Schaghticoke Reservation nearby, and a part of the Appalachian Trail!

Come visit this town and get back in touch with nature! Macedonia Brook State Park is a perfect location for hiking, camping or picnics. Enjoy views of the Catskill Mountains and Taconic Mountains. Or, head out to the waterfall paradise that is Kent Falls State Park. You can even go fishing here and catch the trout brought in from state hatcheries. Head back into Kent to appreciate the antique shops and boutiques, or recharge at the Fife n’ Drum Restaurant.

8. Madison, Connecticut

Madison is located in New Haven County, right on the shore of the Long Island Sound. It was settled in 1641, and declared a town in 1826, making it unofficial rivals with Guilford, the town from which Madison split. Come sneak away to Madison’s beaches for a relaxing, seaside vacation.

Check out Hammonasset Beach State Park for a picnic, nap, or camping. You can fish off the pier here as well. Or, play a volleyball game at Surf Club Beach or take out a sailboat on the water. Enjoy a good meal and unique atmosphere at RJ Julia Booksellers, and pamper yourself at Quiet Cove Massage Therapy. Enjoy a few days at Scranton Seahorse Inn and let the sea breeze rejuvenate you. You’ll feel like a new person.

9. Monroe, Connecticut

Located in Fairfield County, Monroe is close to bustling big cities like New York City, but far enough away that you still have the peace and quiet of the country. The town gets its name from James Monroe, the fifth president of the US. A town that still looks like it is from the colonial times, take a quick trip away and stop here to recharge your batteries.

Bring your bike and hit the trails here – there are many bike paths for aspiring cyclists. Or, stay in town and spend some time becoming a beer connoisseur at Veracious Brewing Company. You can sober up over a cup at Last Drop Coffee Shop before walking around and enjoying the scenic town. Enjoy a good meal at Carl Anthony’s Trattoria and take the time to breathe now that you’ve left your worries behind in the big city.

10. Mystic, Connecticut

Mystic is located in New London County. Mystic is unique – it has no independent government as it is not officially recognized as a separate municipality. A whimsical sounding name, they actually say that “Mystic” was derived from the Native American term “missi-tuk” that referred to a large river, a suitable name given the town’s important seaport in colonial times.

Historically significant because of its seaport, the town has commemorated this history at their maritime museum, where you can see the preserved sailing ships. You can also visit the Mystic Aquarium and Institute for Exploration, or watch beluga whales. Wander historic Downtown Mystic, and enjoy some fresh seafood at S & P Oyster Co. Have a slice at Mystic Pizza, inspiration for the movie by the same name starring Julia Roberts!

11. Niantic, Connecticut

Located on the Long Island Sound on the Niantic Bay, this village is a seaside resort destination. Named after the Niantic People, the tribe inhabited Connecticut and Long Island before the areas were settled by the Europeans. Niantic is ideally situated next to the water and is also surrounded by beautiful nature, making it an ideal vacation spot for anyone.

Come visit and spent some time sailing on the bay. Head out to the mile-long beach at Rocky Neck State Park, or row out to some of the tiny islands dotting the coast, like Gardiners Island. You can camp here in the summer or hike in the woods in the off-season. While a great summer destination, there is something to do here for all seasons. Check out the books at the Book Barn and wander the shops on Main Street. Enjoy a few days off at the Inn at Harbor Hill Marina and let the sounds of the ocean soothe you.

12. Old Saybrook, Connecticut

Old Saybrook is located in Middlesex County, and was founded in 1635 at the mouth of the Connecticut River. The Fort controlled the main trade and supply route to the upper river valley, and the Collegiate School of Connecticut was first chartered in Old Saybrook. The school was later moved to New Haven, was renamed Yale University.

Treat yourself and visit Yale’s birthplace when you make a reservation at Saybrook Point Inn & Spa. Walk along Harvey’s Beach or play a round of golf at Fenwick Golf Club. Check out the Lynde Point Lighthouse or go antiquing at Long Ago Antiques. Enjoy the food at Liv’s Oyster Bar & Restaurant and after, have a quiet drink at Fresh Salt.

13. Putnam, Connecticut

Putnam is in Windham County and was named after Revolutionary War General Israel Putnam. The town grew around the clothing mill industry, and was a key contributor in making clothes for Civil War soldiers. Come visit this small New England mill town.

Catch a show at the Bradley Playhouse, or go antiquing at Jeremiah’s. Get back in touch with your artistic side at Artique – a Paint Bar, or check out the unique instruments at String Tinkers. Relax at the upscale inn, Whitehaven, and sit down for a leisurely eating experience at 85 Main. We recommend saving room for dessert at Victoria Station Cafe!

14. Washington, Connecticut

A rural town in Litchfield County, Washington is a town known for rubbing shoulders with New York City and well known for its lovely countryside, historic architecture and bustling cultural life. Located in the foothills of the Berkshire Mountains, many locals can trace their ancestry back to the Colonial period.

Bring your walking shoes and head out to the Shepaug River which winds through Hidden Valley Preserve. Or, visit the second largest natural lake in Connecticut, Lake Waramaug – bring your camera, it’s very scenic. If you’re staying in town, spend some time at Hickory Stick Bookshop or Hollister House Garden. Put your feet up at the Orange Gild Bed and Breakfast, and treat yourself to an upscale eating experience at the Mayflower Dining Room.

15. New Milford, Connecticut

New Milford is located in Litchfield County, on the Housatonic River. The area was previously inhabited by the Weantinock Native Americans, a subgroup of the Paugusset, who farmed and fished here before the arrival of John Noble in 1707, who established a small community there. The town later participated in the American Revolution by sending the 7th Connecticut Regiment to fight in battles such as the Battle of Brandywine.

Come visit this town and pay a visit to Lovers Leap State Park, or Harrybrooke State Park – both are perfect for either a relaxing picnic or a hike. Pick up a hobby and take a cooking class at the Silo Cooking School, or visit the Village Center for the Arts. Try the sushi at Yokohama or disconnect from normal life at Homestead Inn. You deserve the quiet rest!

15 Best Small Towns to Visit in Connecticut:

• Chaplin, Connecticut
• Colebrook, Connecticut
• Columbia, Connecticut
• Cornwall, Connecticut
• Cromwell, Connecticut
• Essex, Connecticut
• Kent, Connecticut
• Madison, Connecticut
• Monroe, Connecticut
• Mystic, Connecticut
• Niantic, Connecticut
• Old Saybrook, Connecticut
• Putnam, Connecticut
• Washington, Connecticut
• New Milford, Connecticut

25 Charming Small Towns in Connecticut (2024)

Despite being the third-smallest state, Connecticut has a lot of character and charm and offers both locals and visitors a range of experiences.

From idyllic towns boasting picturesque landscapes and rich history, breathtaking national parks , to coastal towns with lots of places to shop, the Nutmeg State is home to lots of hidden treasures.

So, the next time you feel like taking a break, put on your favorite songs about Connecticut playlist and make sure you visit these 25 small towns in Connecticut that are home to sparkling lakes, luscious forests, sandy beaches, and mesmerizing waterfalls.

Mystic is a former shipbuilding seaport, and its maritime history is pretty clear throughout the town.

But you might know this town from Julia Roberts’ famous movie Mystic Pizza!

The town has three historic districts that have a bunch of notable landmarks and is the place to be for those into maritime history.

Start your day at the Seaport Museum , where you can see things like an old whaling ship, a recreation of a 19th-century fishing village, and even a children’s museum.

Then, head over to the Historic Ship Nautilus & Submarine Force Museum to go on the world’s first nuclear-powered submarine.

End your day at the Mystic Aquarium , where you can see penguins, seals, whales, and other sea creatures before getting something to eat at the Olde Mistick Village , an open-air mall in an 18th-century village setting.   

2.  Kent

Kent is the place to go if you truly want to relax while enjoying panoramic views of the beautiful landscape.

Start your day at Kent Falls State Park that’s home to trails, covered bridges, and one of the best waterfalls the state has to offer.

History buffs can head over to Kent Furnace or Kent Historical Society to learn the area’s history.

Follow that up by going to the Eric Sloane Museum , where you can see the artist’s studio, his work, and even his hand tools.

Other notable places to check out include the Macedonia Brook and the Bulls Bridge, one of the few remaining functional covered bridges.

3.  Essex

Essex is one of the best quaint towns in Connecticut with a rich sense of history.

There are a lot of historic buildings and authentic farm structures that date back to the Revolutionary War.

Some of the most famous landmarks include Essex Art Association Gallery , Hill’s Academy , Centerbrook Congregational Church , and the Savings Banks.

The First Baptist Church of Essex, built in Egyptian revival style, is also worth visiting, especially since it’s one of the three present in the country.

Make sure you also take a ride on the Essex Clipper and Essex Steam trains.

And if you plan it right, your kids might even get to see Thomas the Tank Engine.

4. Westport

Westport is aptly known as one of the best beach towns in the country—Compo Beach is absolutely pristine and has facilities for different kinds of water sports, including sailing, stand-up paddleboarding, and kayaking.

And if you want to just relax on the sand, the two most famous spots are Sherwood Island and Old Mill Beach.

The town is also a great place for art lovers— MOCA Westport , a contemporary art museum, boasts programs in performing arts and visual arts, the Levitt Pavilion hosts music shows, and the Museum of History and Culture will leave you gobsmacked. 

Before you head back, go over to Main Street along the Saugatuck River for a shopping spree at big names like J. Crew, Tiffany’s, and Lululemon.

Madison is another seaside retreat and is a great place for outdoor lovers.

The Hammonasset Beach State Park (the biggest state park in the country) and Meigs Point Nature Point offer panoramic views of the beautiful town, while the Shoreline Greenway Trail is a great place for a stroll.

If you don’t like the outdoors too much, you can catch a show at the Madison Art Cinemas, check out the Madison Arts Barn , or visit galleries and cafés.

The town’s New England-style buildings are a sight to see, too! 

6. Old Saybrook

Old Saybrook is one of the best small towns in Connecticut, and it’s not just us saying that!

Many people find this to be one of the most beautiful towns in the state.

Plus, it’s where the famous actress Katharine Hepburn used to live!

So while you’re here, make sure you visit her mansion and the Cultural Arts Center named after herself which hosts numerous performances and theater. 

Before you leave, make sure you hit Main Street too, where you’ll find many independent family establishments.

And history buffs should definitely check out the Old Saybrook Lighthouse.

7. Washington

Washington really has something for everyone, from those who just like to appreciate the colors of the world to history buffs and art lovers.

Once you get here, the first thing on your list should be to go to the Hidden Valley Preserve , where you’ll find the Henry David Thoreau Suspension bridge, which is absolutely a marvel of engineering.

Plus, the view from the top of the bridge is Instagrammable!

Then, hike through the woods to reach the Gunn Historical Museum which has American artifacts and Steep Rock Reservation.

And before you leave, make sure you stop by the Hollister House, a private garden with Japanese accents and unique water features.

8.  Niantic

Niantic is another scenic town that’s been around since even before the 1600s.

When you’re here, make sure to visit at least McCook Point Beach , the Rocky Neck State Park , and the Niantic Bay Boardwalk.

Another thing we like about this town is the collection of funky and unique shops.

On the top of your list of shops to visit should be The Book Barn, which has more than 350,000 titles, including out-of-date and rare titles.

And if you love kayaking, make sure you stop by Three Belles Outfitters–the East Coast’s biggest hobby kayak store.

9.  Putnam

Putnam sits on the bank of the Quinebaug River, so you can imagine how stunning it might be!

It’s a haven for art lovers: the historic downtown district hosts art festivals and has numerous boutiques, galleries, and even antique malls with interesting vintage items.

If you’re visiting with your family, make sure to check the Gertrude Chandler Warner Boxcar Children’s Museum while outdoor fans can indulge in swimming, cycling, and hiking.

10.  Chester

Despite its industrial background, Chester has done a great job at preserving its history and heritage, and that’s clear by the numerous, well-preserved antique buildings and houses present in the center of the town.

Alongside history, Chester also focuses a lot on art.

The budding art scene here includes a theater, boutiques, and numerous galleries.

Its topography is an advantage, too.

You just have to hike a little to enjoy some mesmerizing views.

11.  Greenwich

Think of Greenwich as a small town with the amenities of a metropolitan, making it one of the best small towns in Connecticut to live in.

High-end shops, world-class restaurants, and unique galleries and boutiques—you’ll find everything here.

Nature lovers should check out the Audubon Center (a 300-acre sanctuary), history lovers should check out Bruce Museum , and art lovers have to stop by the Flinn Gallery.

Architects are also in luck—the Philip Johnson Glass House is a must-visit! 

12.  Colebrook

While Colebrook is famous for its 4th of July celebrations, it’s a great place for a relaxing weekend getaway.

It’s particularly stunning in the fall when the foliage is nothing short of stunning.

And the best way to enjoy the scenery is at the Lake Triangle Dam or the Gaylord Pond Dam.

The Haystack Mountain Observation Tower which offers views of the Long Island Sound marine sound and tidal estuary is also worth visiting.

And outdoor lovers can go hiking at the state park.

13. Ridgefield

Ridgefield sits on the foothills of the mountains and looks like something out of a painting. And in addition to marveling at its beauty, there’s a lot to do here!

For starters, you can get a glimpse of history at the Keeler Tavern Museum and then be mesmerized by contemporary art at the Aldrich Museum.

Or you can take a stroll down the Museum in the Streets trail lined with historical buildings to learn more about the town’s history.

Finally, head over to Weir Farm, a national park that’s dedicated to painting.

14.  Litchfield

Litchfield is absolutely beautiful and looks like something right out of a painting.

Here, you can find many scenic locations, like the Topsmead State Forest , which is a great place for picnics, and the White Memorial Conservation Center , the largest wildlife sanctuary and nature center with up to 35 miles of trails.

The town’s historical district is worth seeing, too, especially the Historical Society & Museum.

And before you go, make sure to stop by the White Flower Farm that hosts acres of beautiful display gardens—now that’s something for the ‘gram!   

15. Milford

Milford is a coastal town best known for its beaches, the coastal center of Audubon, state parks, and historical buildings that have been repurposed into shops, boutiques, and cafes, adding to its charm.

It’s less crowded than many other beach towns and is quite charming.

There are lots of activities that you can take part in, too.

For instance, you can head over to Walnut Beach which boasts the state’s longest boardwalks or you can get a rental from the beachfront to enjoy the surf and sand.

Silver Sounds State Park, a 297-acre park with marshes and dunes, is also worth checking out.

And if you find yourself bored, head over to the Milford Cultural Center , where there’s always some event going on.

16.  West Cornwall

West Cornwall is perhaps one of the smallest towns in Connecticut but it’s relatively famous thanks to Cornwall Bridge, a covered bridge, that you might have come across on Instagram.

But even more Instagram-worthy are the gingerbread-house buildings, which is something you might expect to see in a Christmas movie!

Since the town is present on the Housatonic River, it makes for a sight for sore eyes, especially during the fall.

And once you’re done filling up your gallery with all sorts of mesmerizing photos, you can partake in activities like canoeing, fly fishing, kayaking, camping, and rafting.

Or you can go hiking in the Mohawk State Forest .

17.  New Milford

Also lying on the banks of the Housatonic River, New Milford is one of the best little towns in Connecticut.

It not only dates back to the indigenous times, but it’s also home to 12 landmarks that are part of the National Register of Historic Places .

These include Housatonic Railroad Station , Boardman’s Bridge , and New Milford Center Historic District.

When you’ve had your fill of history, you can go for a hike at the New Milford River Trail or visit the Lovers Leap State Park where you can get stunning views of the river and get a chance to visit the industrial ruins that date back decades.

And on Sundays, you can buy all sorts of knick-knacks at the Elephant’s Trunk , which is one of the best flea markets in the state (and the largest in New England).

18.  Monroe

Just like many other towns in Connecticut, Monroe also has strong historical ties.

The town itself is named after America’s 5th president, James Monroe, and is home to numerous historic buildings like the Thomas Hawley and Daniel Basse houses and the Stevenson Dam Hydroelectric Plant.

Meanwhile, the historic district has a colonial-like look.

But the town isn’t only for history buffs; horror fans can also have a nice time here since the town is home to the famous Stepney Cemetry and the Warren Occult Museum.

Plus, there are lots of cycling and hiking trails and even parks ( Webb Mountain Park , Willian E Wolfe Park , Indian Well State Park ) to keep you busy!

19.  Guilford

Guilford is another beach town with lots of places to go, including 16th-century house museums!

When planning a day here, make sure you add the Henry Whitfield House , the Bluff Head peak , and the Metacomet Ridge to your itinerary.

And if you’re interested in learning the town’s 375-year history, you can take the free guided walking tour. 

Bishop’s Orchards and The Place Restaurant (which features tree stumps for chairs and cooks seafood over a fire pit) are pretty famous among tourists and there are lots of picnic spots, too.

And before you end your trip, make sure to check out Chaffinch Island or Jacob’s Beach.  

20.  Cromwell

Cromwell is the place to be if you want to experience authentic old-time New England towns.

The town got its name because of a boat (named after Oliver Cromwell) that sailed the waters of the Connecticut River. 

If you’re here because of its history, you’re in for a treat.

In addition to the Sage-Kirby house (a Federal period black house), there are two historic districts here, the Middletown Upper Houses Historic District and the Main Street Historic District.

After you’re done with your history lesson, head over to the Cromwell Meadows Wildlife Management Park and the River Highlands State Park to fill up your gallery with stunning pictures!

21.  Columbia

Columbia is another great place for history lovers.

Start your day by taking a walk through the Columbia Green Historic District , which is home to numerous historic buildings, including the WW1 memorial, the Congregational Church, and the Town Hall.

You’ll be in awe of all the old stone buildings here.

End your day by taking a hike at the Airline trails and the Hop River.

Or head over to Mono Pond Recreation Area or the train museum!

22.  Chaplin

Chaplin is a quirky place with a bunch of interesting spots for you to visit, such as the Chaplin Museum , the picturesque Diana’s pool on the Natchaug River, and the Witter House.

The Chaplin Historic District is also worth seeing, with its wood frame houses as well as the Congregational Church Building.

Other popular spots include the historic Eaton’s Store and the beautiful library building while a lot of people also opt for taking a trail around town.

23.  Branford

Branford is characterized by coastal landscapes, unlike what you’ve seen before, and family-friendly breweries.

Once you get here, take a cruise around the Thimble Islands, an archipelago of 25 small islands home to summer cottages that were built back in the Victorian Era.

Then, go for a bike ride at the Connecticut Shoreline Trail to enjoy the scenery that the place has to offer before heading over to Stony Creek, a small beach community with a beach and a two-in-one market and gift shop.

24.  Simsbury

We can’t talk about cute towns in Connecticut without including Simsbury!

To make the most of your trip, start from the Drake Hill Flower Bridge covered by vibrant plants before making your way downtown.

Here, check out the Art Trail, where you’ll find a collection of sculptures by John Seward or you can take a bike ride on the Farmington River Trail.

End your day at the Talcott Mountain State Park , especially at the Heublein Tower which provides panoramic views of the whole area.

25. Fairfield

And finally, we have Fairfield, a small, charming town with sandy beaches and high-end restaurants.

In fact, when it comes to beaches, you’re spoiled for choices!

There’s Sasco, Southport, South Pine Creek, Jennings, and Penfield to choose from.

Apart from soaking up the sun on the beach, there are other locations for you to check out, including the Old Post Road Historic District , the Fairfield Museum & History Center, and the Farmer’s Market.

And finally, you can visit the Connecticut Audubon Society Birdcraft Museum & Sanctuary, which is home to lots of interesting birds.

Hey! Want more ideas on the best small towns in the USA? Check these out!

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23 best small towns in connecticut (for a weekend getaway).

New England has no shortage of cute and charming places to visit (especially during fall)! These are some of the best small towns in Connecticut to add to your bucket list!

We have covered several Connecticut small towns ranging from the seaside communities to inland villages and there are plenty more than just these ones on the guide!

You will also find many of these CT towns are easy day trips from Boston , Hartford, and other larger places (even NYC!)

If we missed any charming small towns or cities in Connecticut , let us know in the comments. Thanks!

Best Small Towns in Connecticut

A gem of a village in Long Island Sound, Niantic has been around since before the 1600s.

When in this scenic town, hit the Niantic Bay Boardwalk, the Rocky Neck State Park, and McCook Point Beach for harbor views.

If you’re a bookworm, check out the Book Barn. Three Belles Outfitters is the go-to spot for water sports fans. Speaking of water, you can catch Striper Snax and Black Hawk in the waters here.

Accommodation-wise, we recommend the Harbor Hill Marina inn, which has great food and views.

With a population of less than 10,000, Putnam is an ideal spot to relax.

This New England small town offers sights like the Gertrude Chandler Warner Boxcar Children’s Museum, the Bradley Playhouse, and the Complex Performing and Creative Arts Center.

The Historic Downtown district is popular with art enthusiasts, while outdoor fans can enjoy hiking, cycling, swimming, or simply gazing at the Quinebaug River from Putnam River Trail.

Make sure you also check for any events or exhibitions, as Putnam is full of them!

Looking for a quiet getaway that also comes with beautiful scenery and a sense of history?

Colebrook is home to the Rock Hall 1900s Tudor revival house. There are also beautiful views from sights such as the Gaylord Pond and Lake Triangle dams.

Visit the Haystack Mountain Observation Tower to gaze at the Long Island Sound marine sound and tidal estuary. You can hike up the trail in the state park.

Colebrook is known for the 4th of July celebrations. Visit the Colebrook House for food, and Rock Hall Luxe for lodging.       

Westport is conveniently close to NYC, which means it can be a perfect escape for a weekend!

If you’re a fan of art, the Westport Country Playhouse and the Museum of History and Culture are great places to visit in this quiet town.

It is also beaming with great eateries and shopping locations in its downtown area, which runs along the Saugatuck River.

The outdoor Levitt Pavilion hosts live music shows during the summer season.

The Rolnick Observatory, Burying Hill Beach, and Sherwood Island State Park are also great to visit.    

Greenwich 

Greenwich is one of the richest small towns in CT, as well as one of the oldest.

A short train ride away from NYC, it includes a number of historical buildings such as Bush-Holley, Thomas Lyon, and the Putnam Cottage.

Explore the town further by checking out Greenwich Avenue, Bruce Museum, and the Finn Gallery. Architect enthusiasts should definitely visit the Philip Johnson Glass House.

Fans of nature should not miss the Audubon Center. All restaurants and boutiques here are world-class. The town also hosts the Greenwich International Film Festival.

West Cornwall    

West Cornwall is most known for Cornwall Bridge built in 1762, which you might have seen a lot on social media.

This village is at its peak scenic beauty in fall, while outdoor activities like kayaking, fishing, camping, and canoeing reel in quite the crowd in the summer, including the local population.

You can find a lot of souvenir shops and eateries when in the village to get the real taste of New England cuisines. 

Full of beautiful sycamore trees, Bethel is more than meets the eye.

Home to the headquarters of Duracell and the Greenwood Avenue Historic District, this small town is full of antique stores, local eateries, and farms.

Bethel’s indie movie theater also hosts the annual Connecticut Film Festival. 

Other notable locations are the public library and Blue Jay Orchards. Monster Mini Golf and Laser Tag, Sky Zone, and the Toy Room are all great for children.   

Madison 

A popular attraction in Madison is Hammonasset Beach State Park, the biggest beach in Connecticut (and one of the best beaches in New England ). Meigs Point Nature Center and the Shoreline Greenway Trail are also hit with outdoor fans.

The town’s beautiful New England-style buildings include galleries, music venues, and cafes which often exhibit art from local artists.

The Madison Arts Barn and Madison Art Cinemas host great events throughout the year, so make sure to catch some! 

New Milford

Located in western Connecticut and lying on the riverbanks of the Housatonic, New Milford is a quiet town dating back to indigenous times.

It is home to 12 landmarks listed in the National Register of Historic Places, including Boardman’s Bridge, New Milford Center Historic District, and the Housatonic Railroad Station.

If you’re more of an outdoor person, you can hike the New Milford River Trail.

Top-rated restaurants are the Sanzari’s New Bridge Inn and the B & W Bakery.         

Welcome to Litchfield , a beautiful village that offers the ultimate New England experience.

Around since the mid-1700s, Litchfield is full of scenic locations such as the White Memorial Conservation Center and the Topsmead State Forest where you can also go for picnics.

The area itself is full of historic buildings, most of which are located in the Litchfield Historic District. The Historical Society and Museum cater to history enthusiasts while the local restaurants cater to your taste buds!    

Milford    

The coastal city of Milford almost feels like a painting. It is home to the famous Milford Oyster Festival, which takes place on the third Saturday of each year’s August.

You can also visit the Milford Cultural Center where you can attend different events.

This city is most known for its beaches, its state park , and the coastal center of Audubon. Most of the local cafes, shops, and eaters are revived historic buildings, adding an extra charm to Milford. 

Cornwall   

Named after the famed English county, Cornwall has been around since the early 1700s. If you ever wind up here, check out the Mohawk State Forest which has given this town the “Greenest Town in Connecticut” moniker.

Don’t miss the Cornwall Library with its massive collection of nearly 30,000 items.

The historic Cornwall Bridge, railroad station, and West Cornwall Covered Bridge are notable areas to visit, as is the deconstructionist architectural marvel, House VI. 

The sense of history in Essex is breathtaking. There’s a ton to see in this beautiful town: the famous Savings Bank, Centerbrook Congregational Church, Hill’s Academy, and the Essex Art Association Gallery to name a few.

It is most known for the still-functional Essex Steam and Essex Clipper Dinner trains. If you plan your trip just right, you can even catch Thomas the Tank Engine which is a big hit with children.

For accommodation, definitely go for the Copper Beech and the Griswold inns.   

Named after the 5th U.S. president. Monroe is a quiet town full of curiosities.

Comprising 9 neighborhoods, it is home to a number of historic buildings such as the Stevenson Dam Hydroelectric Plant, the Daniel Basse and Thomas Hawley houses, as well as the Monroe Center Historic District.

If you’re a fan of horror, then rejoice! The famous Warren Occult Museum and Stepney Cemetery are located in Monroe. Ironically, so are 11 houses of worship that you can visit. 

Incorporated in 1836, Chester echoes the industrial era of Connecticut. Here you can find the historic Chester-Hadlyme Ferry, as well as the Beth Shalom Rodfe Zedek synagogue, one of Chester’s architectural marvels.

Despite having an industrial background, the town is surrounded by scenic nature which you can enjoy from locations such as Camp Hazen YMCA and Villa Bella Vista.

Most of the town’s historic buildings are now galleries and restaurants, offering great service and food.

With breathtaking sights to take in at Macedonia Brook and Kent Falls State Parks, Kent is the ultimate town to relax in.

The hiking trails will present you with vistas of Appalachia. the Catskill and Taconic Mountains, as well as 17 waterfalls. If you are an art fan, you can visit the Sloane-Stanley Museum.

Make sure to check out the Bulls Bridge, and the inn of the same name which offers delicious local cuisine! Another recommended eatery is the Ore Hill & Swyft.  

Mystic  

Named after the Pequot term “missi-tuk,” Mystic is a former seaport most known for its three historic districts, many of which include notable landmarks.

If you’re into maritime history, Mystic is the place to be: the massive Seaport Museum, the Charles W. Morgan whaling ship, the Historic Ship Nautilus, and Submarine Force Museum…take your pick!

Mystic is also well-known for the movie Mystic Pizza, and guess what?

You can taste the pizza at the restaurant in the Submarine Museum! We also recommend the Olde Mistick Village mall.

Columbia  

Welcome to Columbia , Connecticut! When you arrive in this beautiful town, make sure to stroll down the Columbia Green Historic District to see the many historic buildings there, including the Town Hall, the Congregational Church, and a WW1 memorial. Hiking fans will enjoy the Hop River and Airline trails.

For loop, trails check the Mono Pond Recreation Area. Hit Trailside Treasure for antiques, and the Main Moose for some great food. There is more to Columbia than meets the eye!  

Washington      

No, it’s not the one from DC! Washington CT not only has beautiful scenery but is also home to a number of historic buildings and attractions.

A must-visit is the Hidden Valley Preserve which includes a bridge named after the famous writer Thoreau, the perfect location for photography!

Hike through the wooded areas, and end up at the Steep Rock Reservation and Gunn Historical Museum for an extra sense of culture and history. The Hollister House is also a popular spot!

Chaplin       

Chaplin may be small, but that’s exactly why it’s a great location to visit and is one of the best small towns in Connecticut.

This little CT town includes interesting locations such as the Chaplin Museum, the Witter House, and a famous pool on the Natchaug River.

Be sure to pass by the Chaplin Historic District which includes beautiful wood-frame houses and the Congregational Church building in the early 1800s.

The old town hall, library building, and the historic Eaton’s Store are also popular!

Old Saybrook

What do you get if you mix Katherine Hepburn and one of the oldest towns in Connecticut? Old Saybrook ! Many claims that this is one of the most beautiful towns in CT, and they’re not wrong.

You can visit Hepburn’s mansion, her eponymous Arts Center, Florence Griswold House, as well as the various galleries.

Hike to the Lynde Point Lighthouse, as well as the Rock Neck State Park. If you like beaches, hit Harvey’s Beach. Local eateries here offer great seafood, so grab a bite for sure!    

This is not only one of the most charming towns in Connecticut, but the US as well!

Located in New Haven County, Guilford is a charming town located on the CT seacoast. There are plenty of places to visit here, such as the five historic house-museums which date back to the 1600s.

The Henry Whitfield House is the oldest one in the entire Connecticut area. Outdoor landmarks include the Metacomet Ridge, Bluff Head peak, and Mattabesett and Westwoods trails.

Also pass by the Bishop’s Orchards for wine, apples, and pumpkins! Guilford is also full of parks where you can have picnics!    

Housing the biggest portion of Devil’s Den Preserve, Weston is the closest Connecticut town to NYC.

Most of the activity here is focused on the Town Center, but there are also three historic districts that you should definitely visit: Bradley Edge Tool Company, Kettle Creek, and Norfield.

In these districts, you can find everything from churches, 18th and 19th-century buildings, and historic houses. There are also 7 parks and open spaces which you can pass by if you prefer the outdoors.

Did we miss any of the best small towns in Connecticut? Let us know your favorite Connecticut small towns below!

More New England Travel Guides

• Day trips from Boston
• New Englandʻs best beaches
• State parks in New England
• Best small towns in Maine

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Megan is a travel blogger and writer with a background in digital marketing. Originally from Richmond, VA, she now splits her time between Frankfurt, Germany and Arctic Finland after also living in Norway, Armenia, and Kazakhstan. She has a passion for winter travel, as well as the Nordic countries, but you can also find her eating her way through Italy, perusing perfume stores in Paris, or taking road trips through the USA. Megan has written for or been featured by National Geographic, Forbes, Lonely Planet, the New York Times, and more. She co-authored Fodor’s Travel ‘Essential Norway’ and has visited 45 US states and 100+ countries.

2 thoughts on “ 23 Best Small Towns in Connecticut (for a Weekend Getaway!) ”

What about Woodbury? We never get mentioned. We have beautiful homes, great restaurants and beautiful scenery. There is also a lot of history here. We’re also the antique capital of CT!

Housing the biggest portion of Devil’s Den Preserve, Weston is the closest Connecticut town to NYC.

Where did you get this from? Greenwich is the closest town to NYC Westonis approximately 30 minutes farther east, with six or seven towns in between it and the NYS border. BTW, you list Greenwich in this article about small towns. If I’m correct there are about 70,000 people in the town, which makes it far from small. Also Mildord has almost 60,000 which should exclude it from this list.

Your list is too big and has too many not small towns, but any publicity good publicity.

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The 15 Most Charming Small Towns in Connecticut

Including the one that inspired stars hollow.

Maybe you’re plotting a cross-country move or perhaps you’re simply eager (read, anxious) to take a weekend-long break from a neighboring big city. Either way, good old CT (also known as the Constitution State) has a whole lot to offer—and it’s not all Vineyard Vines and privileged prep schools. Check out our list of cute and charming small towns in Connecticut, which includes quaint beach towns like Milford and rural gems like Chaplin.  First, you’ll swoon, and then you’ll start looking for a plot of land—or a future vacation spot —with your name written all over it.

12 Lesser-Known (but Totally Charming) Upstate New York Towns You Need to Visit

1. Cornwall

• Things to do: hiking, biking, fishing, water sports, skiing 
• Places to stay: West Cornwall Cabin ($212/night) , Mountain View Getaway ($272/night) , The Beehive Cottage ($90/night)

Bordered by the Housatonic River and settled at the foothills of the Berkshire mountains, this Litchfield county gem boasts loads of natural beauty to boot. In fact, Cornwall is said to be the greenest town in the state (we’re talking about actual trees, not environmentalism)—an accolade that can be attributed to the large portion of the gorgeous Mohawk State Forest that it contains. The town has plenty of historical character—it’s home to one of only three surviving covered bridges in the state—but modern day-Cornwall owes much of its appeal to the abundance of recreational activities it has on offer (hiking, biking, fishing, water sports and winter skiing , to name a few).

• Things to do: historic sights, seaport museum, aquarium 
• Places to stay: Renovated One Bedroom Getaway ($164/night) , Seaside Getaway ($195/night) , Private Carriage House ($293/night)

Mystic—a town situated on Mystic river, a body of water that flows into the Long Island sound—became an important ship-building center not long after its founding in the mid-17th century. Today, however, the town is best known for its archetypal New England vibe, lowkey tourist attractions (i.e., an aquarium, seaport museum and lovely historic district)...and the ‘80s classic Mystic Pizza , of course. Indeed, this charming seaport hits the ‘small town, but not snoozefest’ nail on the head, making it a happy medium between urban dwelling and country life.

• Things to do: historic sights, boutique shopping, water recreation 
• Places to stay: New England Beach House ($212/night) , Breathtaking Bungalow ($148/night) , Beach Cottage next to Silver Sands State Park ($208/night)

This quiet beach town is just a stone’s throw away from New Haven, but you could mistake it for a humdrum suburb at first. Never mind the strip malls on the outskirts of this quaint New England spot, though—once you discover Old Town Milford, a historic district complete with cute, quirky shops and good eats, you’ll experience the real charm of this laid back beach town. Aside from ample opportunity for water recreation, Milford also boasts a seriously impressive “town green,” the second longest in New England, that features multiple memorials—yet another nod to the town’s rich history.

• Things to do: historic sights, recreational parks, biking trails 
• Places to stay: Elegant Country Estate Guest House ($155/night) , Romantic Riverfront Farm House ($275/night) , Peaceful Pinewood Retreat ($315/night)

This town in Fairfield County, CT is on the upswing in terms of population growth, being that it’s within easy driving distance of Bridgeport, New Haven and New York City. That said, Monroe has maintained its small-town feel and historical character. Named after James Monroe (i.e., the country’s fifth president), this Connecticut town feels like a blast from the colonial past. However, you don’t have to be into historical reenactments to enjoy Monroe: This one boasts a number of scenic recreational parks (Webb Mountain, Wolfe Park. Great Hollow Lake) and a ton of bike paths to boot.

• Things to do: boutique shopping, antiquing, farm-to-table dining, outdoor recreation 
• Places to stay: Elegant Country Estate Guest House ($155/night) , Direct Waterfront on Candlewood Lake ($699/night) , Waterfront Lake House ($590/night)

What do PT Barnum, Meg Ryan and Duracell batteries all have in common? A town called Bethel, it turns out. A hop, skip and a jump from New York City, this Fairfield County winner is very small and oh-so quaint. Bethel’s downtown may be pint-sized, but it’s nothing to shake a stick at—you’ll find cute boutiques, antique stores and top-notch farm to table eateries there—and the surroundings are ripe with opportunities for farm visits and outdoor adventures. Plus, some good news for film buffs: Bethel has a super cool indie movie theater and serves as the recurring host of the Connecticut Film Festival.

• Things to do: gallery hopping, cultural attractions, hiking with scenic views 
• Places to stay: Saybrook Point Cottage ($189/night) , Charming Chester Retreat ($178/night) , Tuscan Villa ($514/night)

First settled in 1692, the rural town of Chester is a welcoming oasis, tucked into the scenic hillside of the Connecticut River. Here, the backdrop of your day-to-day will include marinas, lakes, brooks and breathtaking waterfalls...oh, and thousands of acres of state forest, too. Although this Connecticut town is pleasantly quiet and old-timey, it’s certainly not stuck in the past: Once a shipbuilding and mill town, Chester is now a magnet for creatives and boasts many art galleries, as well as the Norma Terris Theater—the second stage of the world-renowned Goodspeed Opera House.

7. Washington

• Things to do: historical sights, hiking, natural attractions, skiing 
• Places to stay: Private Annex ($250/night) , Dainty New Preston Cottage ($261/night) , Waterfront House on Lake Waramaug ($842/night)

This farming community features picturesque landscapes—both farm and forest—historical architecture and plenty of culture. Washington’s proximity to New York City makes it a popular retreat, but the total population of the town is only 4,000—so you can certainly count on a quiet, country lifestyle here. Like some other Litchfield County gems, Washington has the benefit of being located at the foothills of the Berkshire Mountains, where residents can enjoy the scenic beauty of numerous nature preserves, hiking trails, lakes and, of course, easy access to the slopes for some of the best winter skiing. Oh, and did we mention that the state’s tourism office cites Washington as one of the inspirations for the fictional town of Stars Hollow in Gilmore Girls ?

• Things to do: shopping, natural attractions, top-notch dining 
• Places to stay: Saybrook Point Cottage ($189/night) , Renovated Barn ($443/night) , Sunny Cottage with Private Beach ($171/night)

The town of Essex sits pretty in Middlesex County, CT—surrounded on three sides by water and located just miles away from where the Connecticut River empties into the Long Island Sound. In the town center, striking Colonial and Federal-era buildings line the streets, some of which house modern amenities. (Think, a funky-cool coffee shop that makes a mean latte, a carefully curated toy shop and a killer seafood restaurant within walking distance.) Yep, this tiny, tree-lined harbor village can be explored on foot; after that, the surrounding park and conservation lands are sure to keep you busy.

9. Branford

• Things to do: historic sights, beaches, hiking, water recreation 
• Places to stay: Beachside Studio Vacation ($329/night) , Ennis Cottage ($199/night) , Beautiful Beach House with Private Beach Access ($250/night)

Located just six miles east of New Haven, you can file Branford under ‘the burbs.’ But not so fast: This idyllic town is a far cry from the bigger city nearby—and instead of strip malls and business parks, this suburb boasts 20 miles of pristine beach, historic homes, scenic roads and easy cruise ship access to the Long Island Sound archipelago known as the Thimble Islands. (Note: Sailing opportunities abound.) As for outdoor recreation, check out the Branford trail—a 30-mile-long circular trail that takes you on a scenic tour of the town’s lakes, woodlands and wetlands.

10. Westport

• Things to do: cultural attractions, historic sights, beaches 
• Places to stay: Cozy Country Cottage ($225/night) , Cheerful Residential House ($225/night) , Westport Paradise ($370/night)

This charming Connecticut town is among the better-known on the list, primarily as an escape for New York City’s well-to-do. That said, this tight-knit community prides itself on negotiating and reconciling its small-town past with the affluence of its present—a give-and-take that accounts for the quaint, but cosmopolitan vibe of Westport. The Westport Country Playhouse and Westport Museum of History and Culture are just a couple of the town’s enticing attractions for creative types. Bottomline: If you’re looking for a compromise between urban and rural life, and can afford the happy medium, Westport will fit the bill.

11. Chaplin

• Things to do: historic sights, natural attractions, hiking, outdoor recreation 
• Places to stay: Lakefront Cottage ($247/night) , The Sunny Cove Cottage on Coventry Lake ($224/night) , Classic Lake Cabin ($155/night)

Tranquil country living coupled with a particularly stunning historic district set Chaplin, a town in Windham County, apart from the rest. This one is entirely unpretentious and—with a population of less than 3,000—very quiet. (In fact, its location in Northeast Connecticut is known as ‘Quiet Corner.’) Don’t expect a foodie scene here, or any of the other trappings of social-media-city-life for that matter...that said, you’d be hard-pressed to find a more beautiful place to go somewhat off the grid.

• Things to do: natural attractions, historic sights, breweries 
• Places to stay: Artistic Concered Barn ($470/night) , Private Kent Getaway With Views ($285/night) , Victorian Guest Suite ($144/night)

The Litchfield County town of Kent cozies up with the New York border...and chances are, residents aren’t mad about it. Living in Kent means you can book it to NYC in less than two hours, while enjoying considerably more scenic stomping grounds. For starters, there’s Kent Falls State Park, which features many cascading waterfalls along with cute picnic spots and probably forest pixies. (Who knows?) Not to mention Bull’s Bridge—a historic wooden behemoth that arcs across the majestic Housatonic River. Plus, the charming ‘downtown’ area offers everything from quality food to independent bookstores. Oh, and there’s craft beer nearby, too—if you decide to venture out to Kent Falls Brewing, that is.

13. Old Saybrook 

• Things to do: cultural attractions, historic sights, natural attractions, beaches
• Places to stay: Belle Vue Cottage ($158/night) , The Cottage ($93/night) , Cozy Loft Getaway ($171/night)

Old Saybrook was once home to Oscar Award-winning actress Katherine Hepburn and the town’s top attraction is a cultural arts center bearing her name. Beyond that, this gem on the Long Island Sound is known for its unparalleled beauty and New England charm. (Old Saybrook is pretty much the definition of picturesque.) The town also boasts a bustling Main Street, replete with restaurants, boutiques and antique shops, and is in close proximity to quite a few natural attractions—most notably Rocky Neck State Park, a perfect place for birding and hiking, as well as the pristine Harvey’s Beach, which is a family-friendly coastal spot with soft sand and placid, shallow water.

14. Madison

• Things to do: beaches, natural attractions, hiking 
• Places to stay: The Barn by the Sound ($250/night) , Beachy & Bright Carriage House ($150/night) , Seaside Oasis in Madison ($600/night)

Another spot on the Long Island Sound—Madison is prized for its coastal beauty and easy access to destinations for nature-lovers, like the Meigs Point Nature Center and the Shoreline Greenway Trail, a mile-long scenic trail for strolling and biking that attracts locals and tourists alike. When you have had your fill of outdoor recreation, be sure to spend some time downtown to browse the bookstores and assortment of cute boutiques or catch an indie flick at Madison Art Cinema.

15. Niantic

• Things to do: beach and boardwalk, children’s museum, bars and restaurants 
• Places to stay: Retreat Home in Beach Community ($75/night) , Townhouse in Niantic ($145/night) , Coastal Getaway with Porch ($158/night)

In case you missed it, the Long Island Sound is the place to go for a serene visit to a charming seaside village. Niantic, yet another fine option in the region, boasts a lovely bayside boardwalk and (like the neighboring town of Old Saybrook) close proximity to Rocky Neck State Park where you can while away the hours whilst taking in the natural beauty of your surroundings. Best of all, Niantic is an excellent destination for families, since it’s home to the hugely popular Children’s Museum of Southeastern Connecticut—a 5,000-square-foot attraction that promises hours of interactive and educational fun for the younger ones in your party.

Which Connecticut Towns Are Most Like Stars Hollow? 

So you’re a Gilmore Girls fan and are wondering which towns feel most like you’re stepping onto the set of your favorite TV drama? The show’s creator and executive producer Amy Sherman-Palladino shared in an interview that the fictional “Stars Hollow” from Gilmore Girls —a picturesque place where everybody knows your name and your business—was inspired by a visit she took to the small town of Washington, CT (see #7 on our list), where she and her husband stayed at a charming inn and thoroughly enjoyed the New England vibes. Suffice it to say that if you’re looking to channel your inner Rory or Lorelei Gilmore, many of the towns on our roundup are a good fit—but probably none better than Washington. 

The 16 Most Charming Small Towns in New York

Freelance PureWow Editor

The 30 Best Small Towns in Connecticut, Including the One That Inspired Stars Hollow

At the Mayflower Inn & Spa, you'll feel like you're staying at Lorelai and Sookie's Dragonfly Inn.

Every item on this page was hand-picked by a House Beautiful editor. We may earn commission on some of the items you choose to buy.

Perhaps the reason we most love it, though, is its seemingly endless supply of enchanting small towns—including, yes, the very one that Amy Sherman-Palladino herself confirmed inspired Gilmore Girls 's Stars Hollow . Then you have coastal towns with spas on the shoreline, inland villages with state parks perfect for hiking, hamlets with restaurants awarded by both James Beard and Michelin, and a town with so many antiques stores there's an official "Antique Trail." Plus, the shopping can't be beat—especially if you're in the neighborhood of Connecticut's answer to Rodeo Drive.

Scroll on for 30 of our favorite cozy and welcoming Connecticut towns that will make you feel like Lorelai and Rory.

The largest town on Connecticut's "Gold Coast," Greenwich features superb arts and cultural attractions, including the Bruce Museum, four beaches along the Long Island Sound, year-round festivals that cater to various interests (like the annual Greenwich Concours d'Elegance), and the iconic Greenwich Avenue shopping neighborhood (which some have likened to Rodeo Drive). So, skipping it? Big mistake. Huge .

The charming seaside village of Stonington, located in the southeast corner of the state, is known for its mile-long beaches, historic seaside homes, and eclectic shops and boutiques. It's also home to two top vineyards: Stonington Vineyards and Saltwater Farm Vineyard.

Washington has the best of both worlds: a small-town vibe with a very vibrant cultural scene. With a backdrop of the Berkshire Mountains—which truly come alive in the fall—the town is blessed with the dreamiest natural surroundings, including Lake Waramaug and the Shepaug River. There's also the absolutely stunning Mayflower Inn & Spa , even has a European-inspired garden. But the ultimate reason it made our list? Amy Sherman-Palladino herself confirmed that Washington served as the inspiration for Gilmore Girls 's Stars Hollow. (The town even hosts an annual Gilmore Girls festival .) Peek inside The Mayflower—where Amy herself stayed—and you might just see Lorelai and Sookie bantering in the corner.

Mystic is truly beloved—and not just because of the Julia Roberts classic Mystic Pizza. Set on the majestic Mystic River, the seaside village is teeming with that classic New England aesthetic, charming shops, and two of Connecticut's most-visited attractions: the Mystic Seaport and Mystic Aquarium. Plus, it has firmly established itself as a foodie haven, with world-class eateries run by multiple James Beard Award nominees, including the Shipwright's Daughter, a local gem within the darling Whaler's Inn that celebrates New England's fresh food heritage.  

New Canaan does have an adorable downtown, but don't sleep on its arts attractions: Grace Farms and The Glass House. The former offers workshops, concerts, and more on its stunning 80 acres of publicly-accessible landscape. House, meanwhile, is a National Trust Historic Site with a permanent collection of 20th-century paintings and sculptures, plus rotating temporary exhibitions (which in the past have included works by Max Strang, Mark Mennin, and Sekou Cooke).

Old Saybrook

One of Connecticut's oldest towns, Old Saybrook offers a trove of historical and cultural sites—and one of the most beautiful beaches in the state to boot. One of the town's main features is Saybrook Point Resort & Marina, a family-owned, AAA Four Diamond–rated property with luxury accommodations and an award-winning restaurant, Fresh Salt. (Just as good as the food? The ocean views.) If you're a theater and film buff, stop by the Katherine Hepburn Cultural Arts Center—aka the Kate—a theater and museum honoring the late actress, the town's most celebrated resident.

Simsbury is the quintessential New England town, complete with a picturesque downtown filled with historic houses, fine restaurants, coffee shops, and small boutiques. The town is also home to Talcott Mountain State Park, one of the state's top hiking destinations. When you visit, make sure to include a stop at the Heublein Tower, a historic lookout spot that sits 1,000 feet high and offers unparalleled vistas.

Nestled on the banks of the Long Island Sound between New Haven and New London, you'll find Westbrook: a quaint shoreline town with all the beachy amenities. For water sports, zip over to Black Hall Outfitters, a full-service paddle sports center that rents canoes, kayaks, and stand-up paddle boards. But if it's relaxation you seek, there's only one option: Water's Edge Resort & Spa, one of the best in New England. Its vacation rentals have walkout access to the beach, plus there are four restaurants, live entertainment almost every night in the summer, and a full-service spa.

Take a walk on the charming side in Milford's downtown, with its bounty of breweries, restaurants, and water views. Like many Connecticut towns, there's also an outdoor draw: Silver Sands State Park, a public recreation space with beaches, dunes, restored marshland, and a 14-acre bird sanctuary. The town also makes for a pretty magical Christmas destination.

Kent features a superb balance of old and new, quaint and chic, and nowhere is that better on display than at the trio of boutique lodgings known as The Kent Collection . While the Victorian (pictured) is a historic classic, the Firefly Inn is an updated farmhouse-style inn, and the Garden Cottages are cozy and eclectic. There's also plenty to do and see in the great outdoors, including Kent Falls, the Appalachian Trail, and a beautiful covered bridge—one of many across the state.

A prime example of a late-18th-century New England town, Litchfield has a historic central green surrounded by attractive restaurants and shops. Combined with the Horse Crossing signs that line its outer roads, there's a real old-world vibe here. For a New American meal in a cozy atmosphere, stop by At the Corner, an adorable restaurant offering quite the selection of craft beers. For a bit more of a splurge, try the delicious West Street Grill, seen here.

West Hartford

Just west of downtown Hartford, West Hartford offers the best of both urban and suburban experiences. West Hartford Center has been the community's main hub since the late 17th century and features dozens of premiere dining destinations—including the family-run Peruvian restaurant Cora Cora, a semifinalist in last year's prestigious James Beard Awards competition. A visit wouldn't be complete without a stay at The Delamar (pictured), a beautiful boutique hotel with its own on-site restaurant and spa. If you're traveling with children, be sure to pencil in The Children's Museum too—it's a sure hit with hands-on exhibitions and live animals.

If you love fishing—or are a local island lover—Niantic is the place as it offers you access to everything. Not only can you reach prime boating and fishing spots from Niantic Bay, but you're also just a quick cruise away from Plum Glut (10 miles), The Race (10 miles), Montauk (21 miles), and Block Island (27 miles). Of course, if you never leave the docks, the view's not too shabby either.

Known as the antiques capital of Connecticut, this charming New England town is filled with historic homes, antiques shops, classic main street attractions, and more. You're sure to find anything your antiques-loving heart desires in the Woodbury Antiques Trail 's more than two dozen shops. When you've finished a day of shopping, head over to the Salt of the Earth Therapeutic Spa and unwind inside the salt caves.

Branford beckons residents and visitors alike with an array of events and attractions, including quite the range of breweries. ( Stony Creek Brewery , Caius Farm Brewery , and Thimble Island Brewing Company , to name just three.) There's something just off the shoreline too: the Thimble Islands, an ideal setting for boating, kayaking, and fishing. And the town happens to look like this at Christmas. Swoon!

You may have heard of Farmington as the home of Miss Porter's School, the elite prep school attended by Jackie O.—but there's much, much more to see and do here. Numerous parks and trails, the scenic Farmington River, and world-class museums (including the lovely Hill-Stead, seen here) abound—and there's plenty for sporty travelers to do like river tubing and cross-country skiing.

Wethersfield

One of Connecticut's oldest towns, Wethersfield is home to the state's largest historic district. Its classic, small-town main street has a country store, restaurants (including the Charles, pictured here), and shops—not to mention a charming B&B that has been the location for multiple Hallmark Christmas movies . History buffs, don't forget the Webb Deane Stevens Museum: It's where George Washington rendezvoused with the Comte de Rochambeau for the Wethersfield Conference.

Middletown is a vibrant place with an incredible arts and culture scene—the center of which is its Main Street, where you'll find international cuisine, shopping, and entertainment. It's also where town celebrations, like the colorful Pride Parade, take place. If you're staying overnight, check in to the Inn at Middletown, a historic hotel offering 100 well-appointed, freshly renovated guest rooms and suites and an award-winning restaurant.

Famous for its flourishing artists' community, Old Lyme was at the center of the American Impressionism art movement in the early 1900s. In the central village on Lyme Street, you'll find several private galleries, museums, and public buildings—including the Florence Griswold Museum (pictured here), the Lyme Art Association, and Studio 80 + Sculpture Grounds—that celebrate this heritage.

Madison is indeed a picturesque coastal town—just look at this photo—but it also features a pedestrian-friendly downtown with an award-winning bookstore, an art-house cinema, a tea emporium, coffee shops, cafés, restaurants, and boutiques. For access to a private beach, book a stay at the Madison Beach Hotel.

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Nowhere else in America has as many cute little towns as New England. Of all the states,  you’ll find some of the cutest small towns in the tiny state of Connecticut ! In many of these spots, you’ll find historic sites and local charm that perfectly represents that New England aesthetic. 

From cute coastal beach towns to  quaint historical villages, I’ll give you the inside scoop on the cutest small towns in Connecticut that you’ll love visiting.

Table of Contents

Small Towns in Connecticut

A mention of Essex  CT, is the only way to start a list of the cutest small towns in CT. You’ll soon realize why it was voted one of the “best small towns in America.” The small-town charm captivates all who visit to experience a historic riverside town.

Essex is located in Middlesex County, right on the Connecticut River. The river played a huge role in developing the town. It’s famous for shipbuilding that you can learn more about in the Connecticut River Museum . The museum holds maritime exhibitions, shipbuilding artifacts, and, of course, gorgeous views of the river.

One of the best ways to take in the sights of the cute town is by cruise. The Essex Steam Train and Riverboat  provides leisure cruises in the Connecticut River on a historic riverboat. What a way to connect with the town’s past!

After spending time on the waterfront, head downtown and go for a stroll on Main Street. You’ll find lots of cute boutique shops and restaurants established in historic, federal-style buildings. Make sure to visit Truffle Shots , you’ll find some of the best chocolate in the entire state.

And if you’re looking for a place to stay in Essex, consider a stay at the Griswold Inn ! It’s one of the oldest continuously operated inns in the country and its absolutely adorable.

Click Here to Check Prices & Book

A quite quaint beachtown in Connecticut, Niantic has so much charm!! You’ve got the lovely downtown area with its variety of boutique shops and restaurants, perfect for taking a stroll and window shopping. Do you like vintage shops where you can find unique and interesting one of a kind items? Anna Pearl’s Curiosities is one of the best antique stores in the state , and its got an eclectic selection of vintage clothing, antique jewelry, and memorabilia of all kinds.

Need a little sweet treat pick me up? Head to Sift Bake Shop , where you’ll find sweet and savory goodies that are sure to delight, plus coffee, tea, and local spirits, too!

Niantic is home to some of the most beautiful beaches in CT, and the waterfront views should not be missed. Rocky Neck State Park and Hole-in-the-Wall Beach are two of the most popular swimming spots, so if you’re planning a summer Connecticut trip, pack your bathing suit! For a scenic beach walk, be sure to check out the Niantic Bay Boardwalk, any time of year.

Looking for a place to stay in this cute CT town? Book a room at The Inn at Harbor Hill , a boutique property with waterfront views.

Click Here to Check Prices & Book!

A winner of Connecticut’s “Best Small Town” by Connecticut Magazine multiple years in a row, Norfolk is an easy addition to this list. This picturesque town is a popular spot for fall foliage seekers in the state, and it’s no wonder. You’ve got great gorgeous natural scenery and lots of great opportunity to get out in it!

Campbell Falls State Park is home to some of the best waterfalls in the state, and it’s a popular fall hiking spot. Haystack Mountain State Park is ideal if you’re looking for those birds eye scenic views. Plus, you can drive up Haystack if you’re not up for or able to make the hike, so it’s more accessible to all.

Norfolk is home to the Infinity Music Hall & Bistro , one of the top spots in the area for an evening out. The restaurant and live performances in an intimate space means there’s not a single bad seat in the house!

Wondering if there are any good places to stay in Norfolk? The Manor House Inn is almost as idyllic as Norfolk is.

  Many people consider Kent to be an escape from the big city. With just a short train ride from New York City, the bustling metropolis views will quickly transform into lavish natural scenery. The cute town of Kent not only has visual appeal but there are plenty of fun things to do around town.

Kent is located right along the Connecticut – New York border. It gives a huge contrast to the big city because it’s known for its vast natural landscapes surrounding it. Kent Falls State Park is one of the most popular attractions for people visiting the town. The park is home to 17 waterfalls , including the largest in the state. It’s a fun outdoor destination for hiking and sightseeing.

Just like the other Connecticut villages and towns on this list, there are plenty of landmarks in Kent that you don’t want to miss. Have your camera ready as you approach Bull’s Bridge, one of three remaining covered bridges in Connecticut. If you’re a literary fan, you’ll have lots of great reading options in the House of Books and Kent Memorial Library.

Immerse yourself into the friendly community by stopping by the Kent Farmers Market to chat with the locals and shop for fresh produce.

Interested in staying the night in Kent? Check out this gorgeous property with a fire pit near Lake Waramaug !

One of the most darling beach towns in the Constitution State, Westport is a picture perfect CT destination. There are three public town beaches, and Compo Beach is highly regarded as one of the prettiest beaches in the state. The boardwalk is the perfect spot for a coastal walk!

Also in Westport is Sherwood Island State Park , with over 235 acres of scenic beauty to explore. It’s also Connecticut’s first state park, and it’s a popular spot for swimming and picnicking in the summer.

Check out this two-hour Sunset Kayak Tour that would be the perfect cap to the day!

When it comes to where to lay your head at night, consider the lovely Inn at Longshore . You’ve got an onsite restaurant, pool, and you’re within walking distance of the beach – what’s there not to love?

One thing you’ve got to love about Connecticut is it’s cute coastal towns, and New London is one of them. New London has something that’s not so common in Connecticut, however, and that is a beach with soft, white sugar sand!

That’s right, if you’re looking for a place you can put toes in the sand, Ocean Beach Park is perfect. In addition to the beach, you’ll also find a boardwalk with arcade games, restaurants, gift shops, and even an Olympic sized pool! This is a very popular CT town to visit in the summer.

Would you like to stay in your own cozy rental with a fireplace, ocean views, and your own private beac h? Of course, who wouldn’t!

If the name itself doesn’t pique your interest, Mystic will invariably encapsulate an ideal picture of a New England small town. In fact, it ranks as one of the best places to live with lots of people moving in from out of town. It’s one of those places that you don’t want to leave after checking out the great restaurants , cute places to stay , and all-around charm!

Mystic was once one of the most important seaports in Connecticut. Much of the maritime history is preserved in the Mystic Seaport Museum. Exhibitions detail lots of information about its history. And just outside the building are several preserved ship museums, many of which are listed on the National Register of Historic Places.

In a port that built hundreds of ships, you’ll still find boats floating around the harbor awaiting new passengers. Go for a cruise on a historic sailboat or steamship and have unbelievable views of the town’s waterfront against the lush trees in the backdrop.

You might even recognize a few places like the Mystic Pizza shop, featured in the popular Julia Robert’s movie of the same name. And if you like marine life, the Mystic Aquarium is one of the best in New England and home to majestic beluga whales.

Mystic has plenty of options for where to stay, but The Whaler’s Inn is the perfect historic inn to match this historic CT seaport town!

If you like historic Connecticut towns, you’re going to love this one! Guilford was settled in 1639, and it has one of the most precious village greens in the region. You’ll see when you arrive, it is about as charming as charming can be.

One of New England’s oldest landmarks is located in Guilford, and it’s a definite must visit. The Henry Whitfield House was built in 1639 and is a history lover’s dream. It is located just down the street from the Guilford Green!

Visit the Village Chocolatier for some tasty treats, then head to the Guilford Art Center to enjoy local art before heading out to Jacob’s Beach for views of lovely Long Island Sound. There’s such lovely coastal scenery in this area of CT!

Looking for where to stay? Check out the Carriage House at Granite Lodge !

Madison is one of the larger towns on this list, with over 18,000 people living there. But what will really blow your mind is that every year, it receives over one million visitors – a majority arriving during the peak summer season. If you couldn’t figure it out by now, Madison is a cute town with picturesque beaches lining the entire shoreline.

Madison is located on the shore of the Long Island Sound. One of the main attractions is Hammonasset Beach State Park . Of all the big and small towns throughout Connecticut, Madison has the biggest beach, extending for two miles. So even with all the tourist traffic, there’s still plenty of room to sunbathe on the golden sands and go for a refreshing swim in the pristine blue waters.

There’s nothing better than taking a stroll through town to admire all of the cute New England-style buildings. There are several cultural venues highlighting art, music, performance, and more. The shops and galleries are excellent places to see the work of local artisans. And some fantastic shows and events happen at the Madison Arts Barn and Madison Art Cinemas all year long.

You’ve got options when it comes to where to stay in Madison, but you should know it is home to one of the dreamiest bed and breakfasts in the state, The Scranton Seahorse Inn .

Wethersfield

Founded in 1638, Wethersfield has the distinction of being the oldest historic district in Connecticut, and it’s lovely for anyone looking for historical preservation at its finest!

There are several beautifully preserved historic homes in Wethersfield, including the Webb Deane Stevens Museum . The grounds and gardens are absolutely gorgeous at this museum, too.

In fact, there is a historic home in Wethersfield that is also a popular place to stay: The Silas W. Robbins House Bed & Breakfast . This is truly one of the most beautiful places to stay in Connecticut, so if you can swing it, we say go for it!

Old Saybrook

It’s hard to say whether Old Saybrook was as stunning in the past as it is today, but there’s something about the old town charm and landmarks that make it one of the prettiest places to visit in Connecticut today.

Old Saybrook was settled in 1635, making it one of Connecticut’s oldest towns. It’s strategically positioned at the mouth of the Connecticut River as it flows into the Long Island Sound. The position was an ideal location for Fort Saybrook, which now operates as a monument park.

Saybrook has one of the cutest lighthouses in the state called the Breakwater Light. I recommend visiting during the evening to see one of the prettiest sunsets you’ve ever seen. The picturesque scenery could easily become your next postcard.

Old Saybrook has a popular public beach called Harveys Beach, where the views are absolutely phenomenal. A few steps from the coast and you’ll be in the heart of town.

Beautiful colonial-era buildings line the small streets as you make your way to popular attractions like the Katherine Hepburn Cultural Arts Center. Dubbed ‘The Kate,’ the former town hall building now served as a performance venue for concerts and recitals.

If you’re able to spring for it, book the Saybrook Point Resort & Spa !

Glastonbury

If a cute town is what you’re seeking in Connecticut, look no further than Glastonbury . Not only is it a charming town in the present day, but it’s one of the oldest settlements in the United States.

A simple stroll around town will reveal why I had to include it on this list. And be sure to have your camera handy because there are tons of gorgeous architectural structures worth stopping to admire.

 Of all the small towns of Connecticut, Glastonbury has some of the most striking colonial-style houses. There are over 150 homes, some dating back as far as the 1600s – some of the oldest houses in the country.

You can see other unique structures like the beautiful First Church of Christ. This town is a slice of New England heaven!

Don’t rush out of town too soon. Glastonbury is also known for hosting incredible events throughout the year. It’s a great way to mingle with the locals and enjoy some of the longstanding traditions. The famous Apple Fest happens in autumn with the apple harvest. Also, the Glastonbury Art Walk exhibits public art installations all around town for a blend of culture and history.

Looking for cozy boutique inn vibes? You’ll find them at Connecticut River Valley Inn !

One of the most lovely Connecticut towns, Litchfield is a fantastic addition to any CT trip. You’ve got all the quaint small town things to do like strolling downtown, scoping out local history at the Historical Society & Museum and the Litchfield Historic District.

Litchfield is also home to the Haight-Brown Winery , Connecticut’s first winery! Today, you can enjoy the picturesque vineyard views while wine tasting or having a lovely meal at the cafe onsite. In the winter they even offer warm spiced wine that can be enjoyed by the roaring fire. How darling is that?

There are several phenomenal restaurants in Litchfield , so pace yourself! But for breakfast, you’ll want to have booked a room at the gorgeous Litchfield Inn – guests rave about their breakfast!

Visit Putnam in any season, and you’ll be amazed at how beautiful the town is. It’s located in the state’s northeastern region, surrounded by scenic nature. From the lush greenery in the summer to the colorful fall foliage in the fall, take a trip upstate to visit one of Connecticut’s cutest small towns.

Putnam is located along the Quinebaug River. The river is just one of the many natural landmarks. It’s surrounded by extensive forested areas where you can enjoy lots of outdoor recreation—one of the top destinations is the Putnam River Trail. Hiking, biking, and swimming are just a few of the recreational activities you can enjoy.

There are also tons of things to do in town. Putnam is full of art and culture. You can check out popular venues like the Bradley Playhouse and the Complex Performing and Creative Arts Centre for live shows year-round.

Just like many other small towns in Connecticut, Putnam too has exciting festivals that happen annually. Head to Main Street for the car cruise or stick around for the light parade during the holidays.

Looking for places to stay near Putnam? This beautiful lakefront cottage could be perfect!

No, not that one, the one in Connecticut! Washington is a teeny tiny CT town that goes all in on charm. You’ve got so many quaint small things to do, like boutique shopping, perusing local art, enjoying the natural scenery of the area, and more.

In fact, this little town is home to a very interesting museum: The Institute for American Indian Studies . With artifacts and exhibits dedicated to preserving and sharing the history of the native people of the area, this is a definite must visit during a Washington trip. They have a replicated 16th-century Algonkian village that’s particularly impressive.

Interested in staying in the inn that is said to have provided the inspiration for the Gilmore Girls? Then you should book The Mayflower Inn , ASAP!

Small towns in Connecticut cannot get smaller than Cornwall; there’s just over one thousand people living there. It’s a friendly little place with a rural community and the cherished covered bridge landmark. What can be cuter than Connecticut covered bridges?

Cornwall is a former farming town that had a brief moment of manufacturing. Now, it reverted to its roots and remains a quaint little town that’s self-sustainable. It has three main districts, each with its own characteristics. The favorite areas are the West Cornwall commercial district and Cornwall Village.

The most popular attraction in town is the Cornwall Bridge . This cute bridge is also one of the last remaining covered bridges in CT. It was built in the mid-1700s and is still used today. However, most people check it out for photos against the landscape backdrop.

During your visit, you’ll have fun recreational activities available on the Housatonic River. It’s popular for kayaking, canoeing, fishing, and camping. The locals are always hanging out, especially during the warmer seasons.

Stop by West Cornwall to browse the quaint shops full of cute souvenirs or diners serving delicious New England cuisine.

As for where to stay in this area, it’s hard to find a more adorable spot than Cornwall Inn !

Okay, Bethel isn’t one of those small towns in CT with a ton of things to do, but it’s got some cool stuff happening!

Step back in time by heading to the Sycamore Drive In Restaurant , Bethel’s drive in that seems to have been frozen in time. You can go for breakfast, lunch, or dinner, but you should definitely try the house made root beer; the recipe has been a local favorite for 75+ years!

Bethel is also home to Blue Jay Orchards , the 122 acre working farm and orchard where you can participate in idyllic small town activities like apple picking. How fun is that?

Looking for a place to stay in Bethel? Microtel Inn & Suites has free breakfast!

Located in Connecticut’s “Quiet Corner,” Woodstock is an absolutely gorgeous place in the Nutmeg State. Visit historic Roseland Cottage then swing by Woodstock Orchards to see what’s in season for their You Pick items. This is always a classic small town CT activity!

When it’s time to refresh, that’s easy. You’ve got Taylor Brook Winery and Taylor Brook Brewery situated right across the road from one another, so you can sample the flavors of the area easily!

As far as where to stay goes, The Watson Boutique Bed & Breakfast is absolutely lovely, and if you’re planning a CT couples trip, it’s perfect.

Milford is one of the cutest small coastal towns in Connecticut. If it feels like you’re walking around an early English settlement, it’s because it’s one of the oldest towns in the state, with many buildings preserved since they were built. While there are many cool things to do in Milford , there are indeed things that you don’t want to miss.

Milford has a shoreline extending approximately 17-miles. Beaches line the entire coast along the Long Island Sound.

An insider tip: Silver Sands State Park has the best beaches in town that I’m sure you’ll love! It also has the longest boardwalk. The beaches are perfect for sunbathing, swimming, and fishing. If you need a break from the water, head downtown and pop into one of the cute ice cream shops. Grab a few scoops and stroll around town to enjoy the charming New England vibes.

A couple of the must-visit attractions are the Audubon Coastal Center to see all the pretty birds from the observation deck or a quirky site like the PEZ museum. Take advantage of the Milford Welcome Center to find out everything happening around town.

Book a room at this gorgeous beachfront cottage if views of Long Island Sound sound like a fantastic accompaniment for your morning coffee!

Nestled inside the Connecticut River Valley, the town of Chester will quickly become your favorite. Whether driving into town through the lush forest region or cruising in on the Chester/Hadlyme Ferry, you’ll be blown away by its charm the moment you lay eyes on it.

Chester is a historic town, first settled in 1692. With many historic buildings remaining, it looks exactly how you’d imagine an old town in New England. The quiet atmosphere and friendly people make it a relaxing place to visit.

Explore town to experience all that it has to offer – from history to culture. You’ll find many buildings listed on the National Register of Historic Places, including the Old Town Hall for its significance and private residences showcasing stunning architecture.

In fact, you can even stay at The Millhouse in downtown Chester, a beautifully renovated historic millhouse turned upscale lodging!

Hand around Main Street to find quaint boutique shops to explore or dine at award-winning restaurants. Many of the businesses are in preserved 19th Century buildings. Honeycone Craft Ice Cream is a must visit!

Small towns in Connecticut like Chester are popular for arts. There are plenty of art galleries around town showcasing local art talent. And if you’re lucky, you’ll get to attend a live performance showing at the Norma Terris Theater, part of Goodspeed Musicals.

Click Here to Check Prices & Book The Millhouse!

Killingworth

Now, Killingworth is a very small town in Connecticut, but it’s got something that is the perfect example of small town sweetness: a lavender farm! Until you’ve walked up and down the rows of fresh blooming lavender at Lavender Pond Farm , you might not understand what makes this such a spectacular draw, but trust us, it is!

You’ll find other cute small town things to do in Killingworth, like visit lovely Chatfield Hollow State Park and explore! There’s a water wheel, covered bridge, and plenty of great walking trails.

For a unique place to stay, book a room at Chatfield Hollow Inn , a wilderness lodge that provides the perfect spot to enjoy the natural scenery of the area.

There are small towns all around the state, but we’ve tried to round up the very cutest, most interesting for you here. Hopefully this Connecticut small town guide will help as you plan your next trip!

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10 Most Beautiful Small Towns in Connecticut You Should Absolutely Visit

Last Updated on June 26, 2023 by Nikki Jain

Best Small Towns in Connecticut

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Address: Chester, CT

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2: Cornwall

Address: Cornwall, CT

Address: Chaplin, CT

Address: Essex, CT

Address: Kent, CT

Address: Mystic, CT

Address: Madison, CT

Address: Weston, CT

9: Greenwich

Address: Greenwich, CT

10: Old Saybrook

Address: Old Saybrook, CT

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Helping you Find the Best Things to do in Connecticut

The 10 Best Small Towns in Connecticut

You may think Connecticut is just a stop along the way to New York or Massachusetts, but Connecticut has a lot of its own charm and grace to offer. If you already live here, then you may have seen some of it yourself, but in case you are planning a vacation or some time away, maybe even your next big move, then you might find our list of the 10 best small towns in Connecticut helpful!

The best thing about small towns is the community, and the smaller the town, the more people you know.

With locally-owned businesses and smaller companies, there is so much in terms of easy daily routines and meeting new people.

So, whether you want to make a quick trip or a big move , you’ll want to look into these 10 best small towns in Connecticut! We’ve also included suggestions for places to stay if you’re looking to get away for the weekend or you need a home base when checking out the town before your move.

1. Cornwall

 In the County of Litchfield, Cornwall has a wealth of greenery, character, and charm. Just off the foothills of the Housatonic River, Cornwall has been hailed the greenest town in Connecticut.

 The Mohawk State forest is within the town of Cornwall, so that’s where a large portion of their greenery and nature comes from.

The historical character is all in the centuries-old bridges in the state of Connecticut. Today’s Cornwall is bursting with recreational activities like hiking , fishing , water sports, and biking.

If you’re planning a visit, check out the Beehive Cottage for a nice, small-town short stay feel!

2. Mystic, Connecticut

  Mystic is a small town that is nestled on the Mystic River, which flows all the way into the Long Island Sound.

Mystic was an important shipbuilding center before its official founding in the mid-17th century.

The charms of New England can all be found in Mystic , as well as many tourist attractions, like one of the best pizza places in Connecticut at Mystic Pizza, and the beautiful seaport.

Mystic has the perfect mix of country life and small town, urban living.

Want to visit? The Seaside Getaway has a small guest capacity and is right where all the fun is!

3. Milford, Connecticut

  Milford has tons to offer in terms of beach towns. It’s quiet, just by New Haven and the Long Island Sound, and has the small-town charms with the comfort of a populated suburb.

Old Town Milford is the real sight to see, where you can find a maintained historical district with old shops, great food, and all the beach town charms.

Their town green is the second-longest in Connecticut and has memorials and lots of town history.

If you are planning a quick visit to check it out, the New England Beach House is small and cozy!

4. Monroe, Connecticut

 Within Fairfield County, the small town of Monroe is welcoming lots of newcomers. It’s a short drive to cities like Bridgeport, New York City, and New Haven.

Their historical charm has carried on over the years and is the proud namesake of the 5th United States President, James Monroe.

There are tons of parks, like Great Hollow Lake and Webb Mountain, and biking paths to give your legs a rest!

For a quick visit, the Romantic Riverfront Farm House is perfect for a short getaway.

5. Bethel, Connecticut

  Not far from New York City , the town of Bethel was home to Meg Ryan and Duracell batteries.

With a small downtown area packed with boutiques and antique shops, you’ll find their farm-to-table eateries and scenic surroundings to be hard to leave.

Start outdoor adventures at their nice parks, or relax at their indie theater, which is home to the annual Connecticut Film Festival.

No matter how long you visit, you’ll find the Waterfront Lake House to be a wonderful resting place.

6. Chester, Connecticut

 Since 1692, the town of Chester has welcomed all and sits nestled along the hillsides by the Connecticut River. There are beautiful marinas, brooks, lakes , and incredible waterfalls to explore.

Their state forest is also over 1,000 acres. Chester is super quiet, has that old-timey feel, and still makes room for new-age advancements like art galleries and theaters.

It’s come a long way from the shipbuilding, mill town that it used to be, and now presents the world-renowned Godspeed Opera House.

Check out a show, or visit for fun, the Tuscan Villa is great for a family trip!

7. Washington, Connecticut

  Washington is a small town and a farming community with serene, farm and forest views.

Their architecture is well-maintained and as historic as their culture.

It is super close to New York City, so it is one of the nice towns in Connecticut to stop by in, but the country lifestyle may make you want to stay longer!

The town is right at the foothills of the Berkshire Mountains , so if you visit, you can fall in love with the scenic nature preserves, trails , and lakes, and winter skiing slopes !

The Waterfront House on Lake Waramaug is one of their nicest hotels!

8. Essex, Connecticut

 Middlesex County hosts the quaint town of Essex . It is surrounded by water on 3 sides and only a few miles away from the Connecticut River’s junction to the Long Island Sound.

The town’s center boasts old, Federal, and Colonial-style buildings that have been around for years!

But, they have been modernized to meet the times, so now you can stop by amazing coffee shops and wonderful seafood dinners.

Lined with trees and right on the harbor, the town of Essex has parks and conserved lands you won’t want to leave!

The Sunny Cottage with a Private Beach is also an awesome place to stay if you visit!

9. Branford, Connecticut

 Right by the Ivy town of New Haven, Branford is a suburban small town that’s idyllic and scenic.

So, if you want a mix of suburban small towns and shops nearby, but also the more historic and charming feel, then Branford is right up your alley.

The Long Island Sound archipelago is easily accessed, and on the way to the Thimble Islands. They have a long, 30-mile trail that will lead you through Branfords’ woodlands, lakes, and wetlands.

If you plan to visit, you might stay at the Beachside Studio Vacation hotel!

10. Westport, Connecticut

 New Yorkers love to vacation here , that’s how you know it’s good! This small town is a cool escape from big city living or just your normal daily routine.

They mix the small-town old-time feel with a modern, present-day vibe. The Westport Country Playhouse is a popular attraction, as well as the Westport Museum of History and Culture.

So, if you’re creative or just love a good vacation, then you might find Westport to be to your liking.

For a quick visit, the Cozy Cottage in Westport is happy to have you!

 We hope the vacation bells are ringing for you now!

Whether it’s a day trip, change of scenery, extended stay, or permanent move the best small towns in Connecticut are charming, welcoming, and timeless.

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Most Beautiful Towns In Connecticut To Visit

• Key takeaways:
• Connecticut offers a variety of beautiful small towns with charming natural and historic beauty, including Kent, Chester, and Essex.
• These towns provide a range of activities such as hiking, visiting state parks, exploring local restaurants and shops, and enjoying the scenic waterfronts.
• Each town has its own unique character and attractions, making them ideal destinations for day trips or longer weekend getaways.

Besides its delightful New England charm, Connecticut offers a lot of fun things to do that can be seen everywhere, from its picturesque beachy scenery to its forested hills and its rolling farmland to its mountains, rivers, and seaside waterfronts. And there’s no better way to appreciate the state’s signature beauty than by checking out one of its most beautiful small towns—here are some of the very best.

UPDATE: 2023/09/04 13:26 EST BY NICHOLAS MAYAMBA

Connecticut is a lovely New England state with charming small towns that place tourists in the middle of nature. From lush forests to sprawling lakes, this updated article highlights the prettiest towns in Connecticut worth checking out.

Related: 10 Most Beautiful Hikes You Can Do In Connecticut

Famous for its fabulous fall foliage , Kent is a quaint Connecticut charmer whose lush scenery is a sight to behold—and not just when the leaves are at their best and brightest. A lovely town center completes this picture-perfect New England town, while a plethora of nearby outdoor attractions means there’s always something to see and do.

• Things To Do: Macedonia Brook State Park; Kent Falls State Park; Bull’s Bridge; House of Books; Kent Falls Brewing Co.
• Wine & Dine: Kingsley Tavern; Swyft; Sophie’s Restaurant & Bakery
• Stay The Night: The Victorian; Fife Country Inn

Its rolling hills and scenic Connecticut River setting make Chester a quaint rural retreat full of natural and historic beauty. But that’s not all: once a hub for shipbuilding and milling, the picturesque town is now home to an up-and-coming local art and culture scene that’s all Main Street USA charm.

• Things To Do: Gillette Castle State Park; Pattaconk Reservoir Trail; Little House Brewing Company; Godspeed Musicals at the Terris Theatre; Chester-Hadlyme Ferry
• Wine & Dine: The Village Bistro; Grano Arso; Thai Riverside
• Stay The Night: Copper Beech Inn (10 minutes); Boardman House (15 minutes)

10 Westport

The coastal town of Westport is all seafront scenery and colonial charm—and perfectly placed for a road trip to the Big Apple (50 miles away!), It’s the perfect weekend getaway from the city. Brimming with small-town beauty, Westport also has plenty of attractions to entice vacationers who like their R&R with a side of creativity and culture.

• Things To Do: Westport County Playhouse; Westport Museum for History and Culture; Compo Beach; Earthplace; Sherwood Island State Park
• Wine & Dine: Rive Bistro; Little Barn; Pane e Bene
• Stay The Night: The Inn at Longshore; Hotel Zero Degrees (10 minutes)

Colonial charm meets waterfront beauty in the pretty Connecticut town of Essex. The perfect place for both day trips and (long) weekends, visitors will enjoy strolling the picturesque harbor, admiring the historic architecture, and enjoying the fun shops and restaurants in the town center of this cozy rural retreat.

• Things To Do: Essex Steam Train & Riverboat; The Pratt House; Connecticut River Museum; Falls River Preserve; The Pratt House
• Wine & Dine: Scotch Plains Tavern; Carlson’s Landing; Tap Room at The Griswold Inn
• Stay The Night: The Griswold Inn; Old Lyme Inn (10 minutes)

A charming historic district—including the second-longest green in New England —gives the seafront setting of Milford quintessential small-town vibes. Full of character and idyllic beauty, plenty of eclectic shops and eateries are here to keep visitors busy when they’re not out on the water (or simply admiring its beachy beauty).

• Things To Do: Old Town Milford; Milford Historical Society House Tours; Silver Stands State Park; Eisenhower Park; The Coastal Audubon Center at Milford Point
• Wine & Dine: Founder’s House Pub & Patio; Bonfire Grille; Bridge House Restaurant
• Stay The Night: Homestead Inn; The Blake Hotel (20 minutes)

7 Wethersfield

An idyllic natural setting complete with tree-lined streets and lush landscapes makes Wethersfield one of the most beautiful towns in Connecticut—and the rural retreat. But there’s more to this beauty than meets the eye; the small hamlet also has a storied past, evident in everything from its plethora of architectural wonders to its many historical heritage sites,

• Things To Do: The Broad Street Green; Wethersfield Heritage Walk; Heritage Way Bike Route; Heirloom Market; Old Wethersfield Historic District
• Wine & Dine: The Charles; Lenoci’s Italian Kitchen; Kaliubon Ramen
• Stay The Night: Silas W. Robbins House; Goodwin Hotel (10 minutes)

6 Greenwich

Though just a short train ride from NYC, the cozy Connecticut town of Greenwich is all small-town charm: from its historic buildings to its Main Street USA vibes. But Greenwich’s location near the Big Apple also gives it a somewhat metropolitan flair seen throughout its distinctive local shops, boutiques, and eateries.

• Things To Do: Greenwich Avenue and Historic District; Greenwich Point Park; Putnam Cottage Tour; Babcock Preserve; The Flinn Gallery
• Wine & Dine: Le Fat Poodle; L’escale Restaurant & Bar; Elm Street Oyster House
• Stay The Night: Delamar Greenwich Harbor; The J House Greenwich

RELATED: This Quirky Connecticut Book Barn Might Be The Place For Book Lovers

With a location at the foothills of the Berkshires and housing much of Mohawk State Forest, it’s no surprise that Cornwall is famed for its scenic natural setting. And this forested beauty is not just easy on the eyes, it’s an epic outdoor playground, too—complete with plenty of year-round recreation opportunities for everything from biking to skiing.

• Things To Do: Mohawk Mountain Ski Area; Mohawk State Forest; West Cornwall Covered Bridge; Housatonic Meadows State Park; Bike the Western New England Greenway
• Wine & Dine: frank.food company; The Village Restaurant (10 minutes); When Pigs Fly South Southern BBQ (15 minutes)
• Stay The Night: Cornwall Inn; Winvian Farm (20 minutes)

4 Old Saybrook

Quintessential New England waterfront vibes abound in the pleasantly idyllic Old Saybrook . Think all the frills of a harbor town, like timeless charm, scenic seaside beauty, and locally-owned storefronts that make this welcoming community perfect for a day away—or a long (relaxing)weekend stay.

• Things To Do: Harvey’s Beach; Fort Saybrook Monument Park; Visit Essex Village; The Katharine Hepburn Cultural Arts Center; Rocky Neck State Park
• Wine & Dine: Alforno Trattoria; Little Pub Old Saybrook; The Essex
• Stay The Night: Water’s Edge Resort & Spa; Saybrook Point Resort & Marina

RELATED: It's Rumored That Captain Kidd's Famous Treasure Can Be Found On This Connecticut Island

Though the bustling CT town of New Haven is right on its doorstep, the picturesque and pretty Branford has a distinctly charming small-town feel that can be seen everywhere, from its bucolic beaches to its stately homes. From basking in beachy vibes to trekking the town’s scenic trail, this lovely suburb has it all.

• Things To Do: Branford Trail; Cruise to Thimble Islands; Shore Line Trolley Museum; Branford Point Beach; Stony Creek Brewery; Branford Supply Pond Park
• Wine & Dine: Home; Rosso Vino; Mosaico Cuisine
• Stay The Night: Owenago Inn; Thimble Islands Bed & Breakfast

Tourists will be hard-pressed to find a more charming Connecticut town than Mystic. Its rich maritime heritage is evident at every street corner, from the numerous sea-related museums that dot the town to the different annual events honoring boats and pirates. Whether looking to stay on dry land or venture out at sea, there are endless fun things to do in Mystic .

• Things To Do : The Seaport Museum, Olde Mystic Village, The Mystic Aquarium, Historic Ship Nautilus & Submarine Force Museum, Mystic Downtown Marina, Mystic Museum of Art
• Wine & Dine: Mystic Pizza, Trattoria Amalfi, The Mariner
• Spend The Night: Hilton Mystic, Steamboat Inn, Taber Inn And Suites

1 Colebrook

A sweet escape from the rigors of daily urban life, this sleepy town in the Connecticut countryside offers a therapeutic dose of natural beauty and small-town charm. Surrounded by sprawling hills and sparkling waters, Colebrook is the perfect playground for nature lovers and comes to its own during fall when hues of yellow, red, and orange highlight its lushly forested spaces.

• Things To Do: Lake Triangle Dam, Algonquin State Forest, Colebrook River Lake, Peoples State Forest
• Wine & Dine: Barnstormer's Burgers & More, Colebrook Store
• Spend The Night: Days Inn by Wyndham Torrington, Royal Coachman Tavern
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Find Your Own Stars Hollow in One of the Best Small Towns in Connecticut

Connecticut.

If you love the idea of moving to a place that has a great quality of life, a variety of affordable housing options, easy access to major cities, and plenty of natural spaces to explore, then you’ve got to consider moving to Connecticut . Although it’s the third smallest state by area , Connecticut definitely packs a big punch when it comes to wonderful areas to call home. 

From 2016-2020, approximately 109,000 people moved into Connecticut , mostly from New York City, other areas in New York, Massachusetts, and also from outside of the country. Drawn by the lower costs of living, job opportunities, schools, and cultural amenities, it’s easy to see why people are choosing Connecticut as their next home. 

Although Connecticut does have its share of larger cities (Bridgeport, Stamford, New Haven), where the Nutmeg State really shines is in its variety of quaint small towns dotted throughout the state. Residents of these small towns enjoy easy access to large metropolises like Boston and New York City but without the large expenses, traffic, and crime that can come with them. So whether you’re considering a move from a larger city out of state or are just looking for a slower pace of life, why not consider one of the best small towns in Connecticut? 

Big City Living vs. Small Towns in Connecticut

When you choose a small Connecticut town over a larger city, you don’t have to sacrifice all the amenities you’re accustomed to. In fact, you’ll enjoy a better balance because you’ll still be close enough to a big city but get to enjoy quiet small-town life, as well! 

In a small Connecticut town, you can say goodbye to intense traffic jams, high costs of living, lack of affordable housing, and higher rates of crime. In return, you’ll get:

• Close-knit communities
• A family-friendly focus
• Less congestion
• Access to more outdoor activities
• Larger space for the money
• An increase in safety

Small Towns in Connecticut - FAQ

Q: What is the best town to live in CT? A: One of the best small towns to live in Connecticut is Mystic, which is known for its charming New England coastal appeal and the famous Seaport Museum.

Q: What is the quietest town in CT? A: If you’re looking for a quiet place to settle down, consider Colebrook, CT.

Q: What small towns in Connecticut are like Stars Hollow? A: Fans of the TV show Gilmore Girls (and anyone looking for a pretty Connecticut town) should look into small-town living in Essex or Washington.

Cute Small Towns in Connecticut Waiting for You to Call Home

In no particular order, these are our best small towns in Connecticut — perfect for anyone and everyone. Although the U.S. Census designates small towns as those with populations of 5,000 or less, we’ve included towns with populations up to 15,000.

1. Niantic, CT

• Average rent (one-bedroom): $1,600
• Average home value: $406,100
• Great for: Public schools, outdoor activities, jobs, families

Niantic is a small coastal town in Connecticut that sits on both the Niantic Bay and the Niantic River . It’s safe to say, if you always wanted to live close to the shore, this is the town for you. It’s easy to spend time on the water, whether you want to boat, fish, kayak, canoe, or water ski. And everyone knows each other in this community, so you’ll have ample opportunities to get to know your neighbors as a resident. 

As a local, you’ll find it easy to fit into the coastal lifestyle. You’ll be swimming at McCook Beach and enjoying fresh seafood at places like Skipper’s Seafood in no time!

2. Essex, CT

• Average rent (one-bedroom): $1,900
• Average home value: $526,400
• Great for: Outdoor activities, schools, families, cost of living

Essex comes with all kinds of little shops to explore as you take in the quaint charm of its downtown, which includes lots of historic buildings. It’s a safe and family-friendly town that boasts of plenty of parks and beautiful places to walk or ride a bike.

You’ll love grabbing a bite in the Griswold Inn and enjoying all the New England charm you’ve ever wanted. Essex also offers cultural amenities like the Connecticut River Museum and the chance to explore the area on the Essex Steam Train . With concerts on the Ivoryton Green and ample opportunities to get out on the water, you’ll love the small-town appeal.

3. Burlington, CT

• Average rent (one-bedroom): N/A
• Average home value: $418,200
• Great for: Jobs, families, commuting, public schools

Located just 30 minutes outside of Hartford, Burlington offers residents the perfect mix of small-town life with easy access to the bigger city. 

Many folks work in Hartford and enjoy coming home to this cute town, and families love the safe neighborhoods. Since they see very little traffic, they’re perfect for walks, bike rides, and runs at almost any time of the day. The town also offers fantastic views of the northwestern hills and gives residents that small-town feel lots of people are looking for. 

Burlington has a variety of trails to check out, as well, where you can enjoy bird watching or just spending time with loved ones enjoying the natural scenery (especially in autumn). When you’re done outside, make sure to fill up at the Greenhouse Cafe & Tavern or Sabrina’s Restaurant .

4. Cornwall, CT

• Average home value: $536,600
• Great for: Families, public schools, healthy lifestyle

Whether you have a family or you’re looking to start one, you can’t do much better than the western Connecticut town of Cornwall. This quiet area is home to all kinds of outdoor opportunities, like Housatonic Meadows State Park or Wyantenock State Forest , where you can hike and bike along the trails. The rolling hills and easy access to natural areas give kids the chance to get out and explore.

Adult residents will love skiing in the winter and river rafting in the summer, but everyone can enjoy the leaves in the fall. And after visiting the West Cornwall Covered Bridge , make it a point to stop in and check out RSVP restaurant or Frank Food Co. !

5. Chester, CT

• Average home value: $431,200
• Great for: Healthy living, schools, affordable housing, jobs

Chester is an artsy small town in Connecticut that offers residents a welcoming, tight-knit community. It’s located along the Connecticut River and boasts of a downtown area full of boutiques, galleries, antique shops, and locally owned restaurants. 

You can be in state parks exploring the trails or out on the water enjoying boating or kayaking in no time at all.

The public school system is also highly regarded, making it great whether you want to raise a family or are looking to retire. 

6. Washington, CT

• Average home value: $996,800
• Great for: Families, commute time, schools

This small Connecticut town served as inspiration for the fictional town of Stars Hollow in Gilmore Girls . Not only is this cute area full of quaint New England charm, but it’s also close to NYC! You can be in the Big Apple in a little over two hours, which is great for those who like working in the city but don’t like the high cost of living. 

You can also enjoy all the delights that western Connecticut has to offer, including lots of time outdoors. Two popular spots with locals are the Steep Rock Preserve and Mount Tom State Park . And there’s also Lake Waramaug and its pristine camping facilities. If you really want to experience all this quaint, close community has to offer, spend some time getting to know your new neighbors at Luke’s Diner or The Hickory Stick Bookshop .

7. Mystic, CT

• Average rent (one-bedroom): $2,600
• Median home sale price: $430,000
• Great for: Schools, retirees, families, nightlife

Mystic is a coastal town in Connecticut that’s great for retirees. It’s also the spot where screenwriter Amy Jones found inspiration for the 1980s film Mystic Pizza ! You’ll love the slower pace of life that permeates throughout this small town and enjoy lots of opportunities to get out on the water. Whether you want to take up boating, kayaking, swimming, or canoeing, you can do it all in Mystic. 

Residents also love the town’s New England charm and history, which can be seen at the Mystic Seaport Museum and the Olde Mistick Village . It’s also the perfect spot to call home if you’re a fan of seafood, as there’s always fresh fish, oysters, and other fruit of the sea coming in on a daily basis. Make sure you check out The Mariner or the S&P Oyster Restaurant and Bar for the catch of the day.

8. Colebrook, CT

• Average home value: $350,800
• Great for: Schools, families, healthy lifestyle, jobs

Colebrook is located in north Connecticut, close to Massachusetts. If you’re looking for a quiet, rural escape and the chance to have lots of space, this could be the small town for you. The natural beauty is unparalleled here, and as a resident, you’ll have plenty of opportunities to get active and experience the outdoors. 

Whether you want to explore the hiking trails of Algonquin State Forest or enjoy boating or fishing on Colebrook River Lake , if you enjoy the peace and quiet of nature, this place is a great option. 

Although stunning all year, you’ll have lots of chances to see the fall foliage in Colebrook, thanks to its hilly terrain. Make sure to take in the views from the Gaylord Pond Dam !

9. Kent, CT

• Average rent (one-bedroom): $1,950
• Average home value: $512,400
• Great for: Families, schools, commute

If you’re looking for a place to get away from the hustle and bustle and relax in nature, Kent should be on your list of small towns. Located close to the New York border, this idyllic spot is only a little over two hours from New York City and a little under an hour and a half from Hartford. Spend the day at Kent Falls State Park and take in the views atop one of its many waterfalls — a great spot for bringing a picnic or just enjoying the area on foot via the trails. 

Families love the small-town feel of this spot, and residents work to create a welcoming, safe environment for all. Be sure to stop into the popular Fife ‘n Drum Restaurant !

10. Old Saybrook, CT

• Average home value: $552,900
• Great for: Retirees, weather, safety, water activities

Another fantastic coastal Connecticut town is Old Saybrook. This town was once home to actress Katharine Hepburn , whose legacy is apparent in the cultural arts center that bears her name and houses performances and exhibits of all kinds. Another interesting part of this town is the lighthouse that’s located on Lynde Point , which draws visitors all year who marvel at the pristine natural beauty of the coastline.

Rocky Neck State Park and Harvey’s Beach offer folks a place to get out and experience the outdoors first hand. And foodies will rejoice knowing there are all kinds of small restaurants to try like Liv’s Oyster Bar & Restaurant and Little Pub of Old Saybrook.

11. Woodbridge, CT

• Average home value: $571,000
• Great for: Jobs, public schools, families, young professionals

Located just a short drive from New Haven is the quiet town of Woodbridge. This is the place to be if you’re working in New Haven but want more space, less crime, and a less expensive way of life. Surrounded by beautiful wooded areas, you’ll enjoy green spaces throughout the town, such as Alice Newton Street Memorial Park , Sperry Falls Park , Elderslie Preserve , and the Old Derby Trail . 

If you want to raise a family, you’ll be happy to know the schools in Woodbridge are top notch. To get a taste of bigger city life with an amazing array of shops, restaurants, boutiques, and bars, New Haven (and the Yale campus) is less than 20 minutes away!

12. Litchfield, CT

• Average rent (one-bedroom): $1,300
• Average home value: $444,900
• Great for: Nightlife, cost of living, families, schools

Litchfield is a quintessential New England town that takes pride in its history and has a welcoming and safe community. The famous author and abolitionist Harriet Beecher Stowe was born here, and it is also home to the first law school in the country . 

Residents enjoy being close enough for day trips into New York City (just under 3 hours) but far enough away to enjoy the pristine countryside. If you love getting out and exploring, you’ll enjoy visiting Topsmead State Forest and trying out new spirits at the Litchfield Distillery .

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Editor’s note: Monthly rental prices were rounded to the nearest $25 and home values were rounded to the nearest $100 for ease of reading.

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The 12 Most Beautiful Towns in Connecticut

Despite being one of America’s smallest states, Connecticut has an abundance of historic towns, charming little villages and areas of extraordinary natural beauty. Known for its peaceful character, friendliness and beautiful scenery, these towns in the state are not to be missed.

Architectural Landmark, Historical Landmark

A tiny town in the Litchfield Hills in Connecticut, Cornwall is famous for having one of the few covered bridges in the area. It’s built from striking red timber in the 19th century, and still serves as an integral part of the town’s infrastructure – as well as being a popular attraction. The town itself features several gingerbread house-like buildings, along with an abundance of trees and greenery, which create a beautiful carpet of reds, oranges and browns during the fall.

A classic small New England town, Chester has its roots in shipbuilding and milling, a heritage for which it’s justly proud, and much of this architecture has been carefully preserved. Chester is also notable for its burgeoning cultural scene, with numerous art galleries, boutiques and the local theatre adding to the charming small-town feel. Beyond the main streets lies a beautiful landscape of hills, streams and forests – all accessible by hiking trails from the town.

Known as the top foliage town in the whole of New England, Kent offers a stunning landscape of lush meadows, winding trails and trees decked in green or autumn colors. As well as a charming center featuring antique shops, boutiques and quirky little cafes, Kent is also home to two state parks: Macedonia Brook State Park is a perfect destination for the enthusiastic hiker, with hilltops looking onto the Catskill Mountains; while Kent Falls State Park has an abundance of waterfalls. The quaint town surrounded by gorgeous scenery makes for a perfect New England spot.

A perfect blend of wonderful heritage and natural beauty, Milford is a must-visit town in the southern region of Connecticut. Less touristy than some of its cousins, Milford has retained its unspoilt, authentic character, while also boasting various charming spots. The center of the old town has many historical buildings and walks, as well as cafes, boutiques, and booksellers, perfect for browsing and relaxing. Milford has large, peaceful outdoor spaces, including the second-largest green in New England – along with idyllic beaches and seafront walks.

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One of the main towns on which Stars Hollow was based in Gilmore Girls , Essex is full of charm, having retained many of its historic buildings. These include a number of farmhouses dating back to before the Revolutionary War, 19th-century Federal-style mansions and the First Baptist Church of Essex – one of only three Egyptian Revival churches built in the United States. The town has a friendly and welcoming community, with a number of inns, shops and galleries. There’s also the Essex Steam Train, an original 19th-century railway and locomotive that tours around the nearby towns.

Just 40 minutes by train from central Manhattan, Greenwich is the perfect getaway from the hectic rush of city life and a popular place for commuters in search of a quieter life. The town is comprised of several areas, each filled with historic buildings, charming inns and quaint local museums – all paying homage to the area’s heritage and culture. Thanks in part to its commuter population, Greenwich has more of a cosmopolitan feel than other local towns, with Greenwich Avenue in the center home to brand names and designer boutiques, as well as more quirky independent shops.

Old Saybrook

Katharine Hepburn’s old stomping ground – the actress lived on the outskirts of the town – Old Saybrook is the perfect waterside New England getaway, with impressive architecture, idyllic natural beauty and friendly locals. The town has many remarkable buildings, from the old-fashioned Saybrook lighthouse to impressive historical manor houses, as well as a soda fountain installed in 1896. A community town, its focal point still lies in Main Street, where numerous independent, family-owned shops vie for attention with original storefronts.

Located on the coast just 50mi (80km) north of New York City, Westport has some of the most stunning scenery in Connecticut. The seafront is comprised of a row of beautiful red-brick buildings, the warm colors contrasting with the sparkling blue of the sea. The seafront is particularly striking during sunsets, where the light casts a wonderful warm glow onto the houses and their reflections in the water. Further into the main town, old-fashioned board houses and impressive buildings dating back to colonial times line the streets, interspersed with large, fresh green spaces – perfect for lazy strolls and picnics.

Wethersfield

Wethersfield has an impressive historical district with over 1000 buildings dating back to 1634, mostly from the 17th, 18th and 19th centuries. The district includes three listed buildings on the National Register of Historic Places, Buttolph-Williams House, Joseph Webb House and Silas Deane house, all outstanding examples of well-preserved colonial architecture. Wethersfield’s abundant natural beauty also sets it apart – the Wethersfield Cove is an idyllic little inlet bordered by lush trees and landscape – with peaceful meadows and narrow winding walks lined with towering trees are dotted around town.

One of the main draws of Madison is the popular Hammonasset Beach State Park , which has two miles of beach, wetlands, woodlands, a boardwalk and nature centre. Its charming downtown area is pedestrian-friendly with a number of restaurants, caf é s, boutiques and The Audubon Shop. A popular haunt is RJ Julia Booksellers, praised as one of the best independent bookstores in the country. In the past it has hosted famous authors such as Anne Rice and Hillary Clinton. Make sure to stop by the Madison Art Cinema, Madison Green Historic District and the Deacon John Grave House. Recommended by Christy Taylor .

Named after Lyme Regis in England, this beach town is famous for its past and present connection to the arts. In the early 1900s it was home to an artists’ community at Florence Griswold’s boarding house and the burgeoning American Impressionist movement. Today it has an art school, many galleries and still attracts practising artists. Located some 10 minutes from town is Sound View Beach, which is accessible to the public (unlike others which are private), where visitors can swim, enjoy homemade ice cream at Old Lyme Ice Cream Shoppe or ride the carousel. Recommended by Christy Taylor.

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17 Best Places to Visit in Connecticut

Written by Shandley McMurray Updated Sep 16, 2022

Connecticut is a natural wonderland packed with some of the country's most inspiring landscapes and a slew of picturesque places to visit. From crashing waterfalls to sparkling lakes to verdant forests to sprawling golden beaches, there are so many memorable things to do in Connecticut .

In addition to its organic wonders, Connecticut is packed with charming small towns that exude New England charm; maritime villages that beg you to jump on a fishing boat; and larger cities that boast excellent attractions like museums, vibrant arts scenes, and fabulous restaurants. No matter what you're looking for, you'll find it in this East Coat gem.

With so many interesting spots to choose from, it can be hard to pick your destination. Whittle down your choices with our list of the best places to visit in Connecticut.

3. Hartford

4. old saybrook, 5. hammonasset state park, 6. stamford, 7. greenwich, 8. silver sands state park, 9. gillette castle state park, 10. new haven, 11. lake compounce, bristol, 12. westport, 13. stonington, 14. the henry david thoreau footbridge, washington, 15. enders falls state park, 16. new london, 17. wethersfield, map of places to visit in connecticut.

The Mystic River gently laps the shores of this lovely maritime village, which is dubbed one of the best small towns in Connecticut . The shimmering water draws attention to the town's storied history as an important port, and multiple attractions teach visitors about its past.

All types of vessels, including massive whaling ships, sailed through and docked at Mystic Harbor. You can see replicas, as well as some refurbished originals, at the remarkable Mystic Seaport Museum . With so many great things to offer (i.e. a 19 th -century seafaring village , children's museum , and the Charles W. Morgan wooden whaleship ), this vast spot deserves a full day of your time.

While in Mystic, book a cruise on the Argia , a two-masted Gaff Topsail schooner, to spot the massive yachts, coastal homes, and sailboats dotting the horizon.

Then, hit the Mystic Aquarium . One of the top places to visit in Mystic , this impressive venue is also one of the best tourist attractions in Connecticut .

Before heading home, stop for a meal and some retail therapy at the unique and picture-perfect Olde Mistick Village , an outdoor mall set to look like an 18 th -century New England village.

We've found the cure for stress. Hint: it's in Kent. Serenely nestled a mere two hours from bustling New York City, Kent is the place where worries disappear. Home to the picturesque Bull's Bridge , one of only three covered bridges in the state, and two gorgeous Connecticut state parks ( Kent Falls and Macedonia Brook ), Kent takes bucolic to a new level.

The small town itself is adorable, chock full of charming shops, cafés, and restaurants. It offers a perfect place to unwind and enjoy a sunny afternoon. Don't miss the darling House of Books , an enchanting bookstore on Main Street that dates back to 1976.

Kent's true beauty, however, lies just outside its border, within the rolling Litchfield Hills . This is where your face will be brushed by mist from one of Connecticut's best waterfalls , Kent Falls . It's also where your ears lulled by the crashing sound of water cascading down Macedonia Falls and your feet massaged by rocks lining the trails through Kent's miles of wilderness.

Connecticut's pretty capital boasts an impressive watery backdrop. Sitting on the banks of the Connecticut River, Hartford was once known as the House of Hope. Today, this large city (one of the oldest in New England) is a wonderful place to soak up a little nature and culture.

The top attractions in Hartford include the Mark Twain House & Museum, the State Capitol, the Connecticut Science Center , and the impressive Wadsworth Atheneum Museum of Art .

Elizabeth Park is more than worthy of a visit. Sprawling across more than 101 acres through West Hartford and Hartford, this delightful space features a phenomenal rose garden and a sweet little Pond House Café .

Speaking of natural beauty, don't miss a trip to Bushnell Park . The oldest public park in the country , its best to visit during spring when the cherry blossoms are in full bloom.

Lovely Old Saybrook is one of the most beautiful beach towns in Connecticut . Harvey's Beach is its main attraction, with its fine sand and calm surf. The Lynde Point Lighthouse , though, is deemed by many to be more picturesque – it's been photographed a bazillion times.

One of the oldest towns in the state, Old Saybrook overflows with charm and enticing antique shops you can't ignore. The background is picture-perfect, especially in the Fenwick Historic district , one of Old Saybrook's top attractions , which boasts shingled cottages dating to the 19 th - and early 20 th centuries.

Katherine Hepburn once called this quaint town home, a fact never to be forgotten with the cultural arts center named in her honor. The Kate , as it's known to locals, features concerts, films, comedy acts, and other great entertainment year-round.

The shining star of Madison , Hammonasset State Park is a must-see. Home to the largest beach in the state – it runs two miles in length – this lovely park is also one of the most popular places to visit in Connecticut .

The park was opened in 1920 and has been a popular attraction ever since. Quite crowded in the summer, especially on a weekend, it's best to hit the beach early, so you can enjoy all it has to offer.

From walking on the boardwalk to cycling to hiking to swimming to SUPing to fishing, there's plenty to keep everyone occupied near this fine sandy shore.

Want to stay even longer? Book a night or more at one of the park's campsites. While in the park, don't miss the Meigs Point Nature Center , an inspiring spot, where wildlife lovers can explore saltwater marshes and spy captivating birds and other creatures.

More business oriented than most other Connecticut towns, Stamford has a lot of things to do for those who shy away from the Fortune 500 Companies that use it as a home base. Yes, you'll find tall office and condo buildings here, but with this cosmopolitan atmosphere comes a lot of cultural pluses.

The Stamford Museum & Nature Center offers historic education in a serene natural setting. Kids will love the bespoke playground. Where else can you perch in a human-sized bird's nest?

The Avon Theater sits downtown, on the popular Bedford Street , just a couple of minutes' walk from Stamford Town Center . You can watch independent and foreign films here to up your sophistication meter.

Harbor Point has been newly revamped, brightening the South End district. Home to its own waterfront, parks, shops, and restaurants, this section has become an exclusive little hamlet.

You'll be hard-pressed to find even one blade of grass out of place in Greenwich. A posh commuter town (NYC is only an hour away by train), this pristine city is one of the most prized (and largest) on Connecticut's Gold Coast. Once here, it's easy to see why it gets so much hype.

In addition to its grandiose, gated homes; immaculate gardens; and sparkling coastline, Greenwich is home to historical gems like the colonial Putnam Cottage , Greenwich Historical Society , and Bruce Museum ; all are family-friendly attractions worthy of a visit.

Perfectly intertwined with these cultural mavens are Greenwich's real shining star attractions : the 147-acre Greenwich Point Park (the view of Manhattan's skyline is unbeatable from this golden beach) and the serene Greenwich Audubon Center (home to miles of trails and a ton of wildlife).

Looking to flex your shopping muscle? Head to Greenwich Avenue . The city's adorable main street is speckled with high-end shops like Sax Fifth Avenue , Lululemon , and Vineyard Vines . When hunger pangs hit, fill up on Italian fare at Mediterraneo , enjoy a curry at Thai Basil , or dine in style at Le Penguin .

Beaches and boardwalks and wildlife, oh my! There's so much to see and do at Silver Sands State Park. Walk along the trails, jump in for a swim, build a sandcastle, gather shells, or try your hand at fishing. No matter what activity you choose, you won't be bored at this lovely state park located in Milford .

While you're here, why not try your luck treasure hunting? According to legend, Captain Kidd hid his valuables on the beach in 1699, and they've never been claimed.

You'll have to wait until the tide is low to walk across the sand bar to Charles Island , the believed hiding spot of this supposed treasure. While you're here, check out the incredible birdlife at the sanctuary located on the island. But be sure to leave before the tide comes back in, or you'll be stuck there overnight.

Gillette Castle serves as the crowning glory atop the southern hill of the Seven Sisters. Designed by William Gillette, a famous actor and playwright between 1914 and 1919, the castle is a true marvel. It boasts interesting wooden locking mechanisms, built-in couches, secret panels, and mirrors set up so the actor could spy on his visitors from above.

The most enjoyable way to reach Gillette Castle is by boarding the Chester-Hadlyme Ferry from the sweet town of Chester , one of Connecticut's most charming small towns. While the ride lasts a mere five minutes, visitors reap spectacular views of the Connecticut River, especially during the colorful autumn months.

With 184 acres of beautiful landscape, a unique 24-room mansion/castle, and a remarkable set of walking trails (they include wooden trestles, tunnels, and a narrow gauge railroad), it's no wonder visiting Gillette Castle State Park remains one of the top things to do in Connecticut.

A coastal town most famous for being home to Yale University , New Haven presents a wide array of fun things to do .

Soak up the culture at the Yale University Art Gallery . You'll find inspiring works by the greats like Van Gogh, Picasso, and Degas. You'll also spot ancient artifacts and creations from talented modern and contemporary artists from across the globe. The best part? Admission is free.

The university is also home to the well-loved Peabody Museum of Natural History , Yale Center for British Art , and Beinecke Rare Book & Manuscript Library .

At the center of town lies the vibrant New Haven Green , which is hugged by the faux-Gothic, Victorian, and more modern university buildings. It's around here that you'll find many of the area's quirky shops and restaurants. It's also one of the best places for photographers looking some good photography spots in New Haven .

A visit to Wooster Square (on the east side of town) won't disappoint, especially if you visit during the annual Wooster Square Cherry Blossom Festival in late April.

If you require a side of thrills with your Connecticut getaway, Lake Compounce is the place for you. The oldest continuously operating amusement park in North America , this family fun zone is a major hit with kids and adults of all ages.

Boulder Dash is a must-ride wooden roller coaster that's been voted top in the world . Be prepared, it gets bumpy! If you're feeling the need for speed, hit the Phobia Phear Coaster, which gets up to 65 miles an hour.

Then, cool off in the water park (the biggest of its kind in the state). The Croc-O-Nile lazy river is super relaxing while plunging down the waterfall at Mammoth Falls will get your heart pumping. Storm Surge is another must if you like excitement. This fun lighthouse waterslide comes complete with lights and sound.

Address: 186 Enterprise Drive, Bristol, Connecticut

Official site: https://www.lakecompounce.com/

Westport is less pretentious than Greenwich, with as much charm as a typical small, New England town. Its affluent nature serves up a hearty dish of high-end shops (like Lululemon , Vineyard Vines , and Tiffany's ) and an even larger plate of upscale restaurants.

The Spotted Horse , Pink Sumo , and The Whelk are just three tasty options. For lighter fare, check out the uber-healthy, delish, and locally owned, Granola Bar .

Wandering through the streets of town is almost akin to being on New York's Upper East Side, without the pungent smells, pollution, or noise. Oh yeah, you'll also reap the added bonus of spectacular scenery and friendly locals.

The Saugatuck River winds its way through the heart of town, passing the popular Bar Taco Restaurant , winking at Main Street , and skimming the newly revamped (and uber-impressive) Westport Library . Stand near it long enough, and you'll spot an ibis, snapping turtle, or swans. Don't miss a show at the Westport Country Playhouse , one of Westport's best attractions .

At the south edge of town lies Westport's pristine and super soft, sandy Compo Beach . While this beach is reserved for town residents and beach pass holders, visitors can buy a day pass for $45 on weekdays or $70 on a weekend.

Sherwood Island State Park is also in town, offering another great beach option for visitors.

Stonington may be small (it measures less than one square mile), but what it lacks in size, it more than makes up for with charm. Founded in the early 1660s, this maritime town sits on the outskirts of Mystic (about seven minutes away by car).

Stonington boasts an adorable main street peppered with shops, cafés, and restaurants. A short walk will get you to the Stonington Harbor Lighthouse , which has stood stoically for more than 170 years, tucked quietly behind a white picket fence off Water Street . Around the corner lies Stonington Point. From here, you can spy three states–Connecticut, New York, and Rhode Island.

A few meters away lies duBois Beach , a small, protected, and sandy spot that's perfect for swimming. During the summer months, the beach is guarded, but expect to pay a small fee to enter. And be warned, there are no concession stands or facilities.

It's not surprising to hear that the Henry David Thoreau Footbridge is one of the most photographable structures in Connecticut . This 120-foot-long suspension bridge is a stunner, especially if you visit during fall. The bridge was built to allow pedestrians to cross the Shepaug River and offers incredible vistas. Look closely, and you'll see the philosopher's most famous quotes carved into the rails.

Named after the famous 19 th -century philosopher, this intricate bridge is tucked into the Hidden Valley Preserve, a natural wonderland located in Washington. Visitors spend most of their time hiking the wooded trails and hillsides of this 727-acre preserve, which is open from sunrise to sunset year-round.

The most popular trail in the preserve is the Winters Hunger Pinnacle . Set aside a few hours, as it is over seven miles long and gets as steep as over 900 feet.

Insider's tip: Goshawks tend to nest both north and west of the footbridge between April and June. Warning signs are posted at this time, and some trails may be closed to protect the birds.

The main reason to visit Enders Falls State Park can be found flowing freely, and serenely, near its center. Enders Falls is one of the best waterfalls in Connecticut . A series of five waterfalls, this glorious spot will help melt your worries away. Watching the water cascade to its final resting place, an inviting swimming hole, is meditative and refreshing.

The park itself is comprised mainly of woodland but is zigzagged with trails that entice visitors to hike through its vast expanse. With over 2,000 acres to explore, you'll want to stay for a while, so it's best to pack a few snacks and water.

Not a real outdoors person? Don't worry. The trails are well maintained and easy. Wear comfortable shoes, and you shouldn't have a problem, unless you don't watch where you step while you're snapping photos of the splendid scenery.

Once a busy whaling Port, New London is now best known as the home of Ocean Beach Park . A giant outdoor wonderland, this park boasts an Olympic-sized swimming pool, waterslide, playground, arcade, mini golf, and concessions.

The town itself harkens back to days of yore, with its charming buildings (some date back to the 1790s) and the U-shaped historic district that highlights the downtown core and sits at the mouth of the Thames River .

Other popular tourist attractions and things to do include taking a Cross Sound Ferry Lighthouse or Mystic Whaler cruise , sniffing flowers at the Connecticut College Arboretum , and visiting Fort Trumbull State Park to learn about the area's maritime history and glimpse a lovely view of the river.

As soon as you step foot in the adorable town of Wethersfield, you'll understand how it got its nickname: "Ye Most Ancient Towne." Founded in the mid-1630s, this historic town presents visitors with a chance to slow down and enjoy a day or two in a time when playing in nature was the best form of entertainment.

Located just south of Hartford and over eight miles from neighboring Glastonbury, this is likely the most charming New England town in Connecticut. More than 150 of its homes and buildings have been around since the colonial times. They lie in Connecticut's largest historic district and include museums, shops, restaurants, and other places worthy of a visit.

The Wethersfield Heritage Walk is three miles long and one of the best things to do in this quaint town. It passes the First Church of Christ , Hurlbut-Dunham House , Buttolph-Williams House , Webb-Deane-Stevens Museum , and Cove Park , among other important attractions.

If you're feeling hungry, stop for a healthy and delicious bite at Heirloom Market . It's set in the old, Comstock, Ferre & Co. building. Inside, you'll find a grocery store selling local, organic groceries and Baker Creek's heirloom seeds. There's also a café serving tasty dishes, juices, and coffees.

More Related Articles on PlanetWare.com

Other Places to Visit in Connecticut : Let's face it, there are a ton of great attractions in Connecticut – way more than would fit on our list. When you're finished checking out the awesome spots mentioned earlier, check out these spectacular waterfalls , jump in one of these sparkling lakes , or laze about on one of these sandy beaches .

The Best Places to Visit for a Weekend in Connecticut : Some Connecticut marvels are too wonderful to see only fleetingly. Schedule at least two days for sightseeing in these popular weekend getaways .

More on Connecticut

Connecticut Just Wouldn't Be The Same Without These 6 Charming Small Towns

Lisa Sammons

Lisa loves animals and has dogs, rats, cats, guinea pigs, and snakes. She is passionate about animal rescue and live music - traveling across the country to see a favorite band is a pretty regular occurrence! Being out hiking in the woods enjoying the scenery with her beloved dogs is another favorite hobby, and also checking out the Pokemon Go scene in whatever city she happens to be in at any given time (coffee and dog leash in hand). You can reach Lisa at [email protected]

More by this Author

There are some great larger cities in Connecticut. A weekend trip to Hartford or New Haven will give you almost limitless things to do. But the heart and soul of the Nutmeg State lies in our small towns, and we have so many wonderful small towns in Connecticut. Whether you’re looking for wonderful getaways in nature, want to explore the history of the area, or are simply wanting to enjoy a quintessential New England small town, these six small towns in Connecticut make for excellent day trips:

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There are so many great small towns in Connecticut that we could’ve gone on and on with this list. Did we miss your favorite? Share your suggestions in the comments – who knows, maybe you’ll see them featured in a future article!

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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Small towns in connecticut.

• Which small towns in Connecticut are bucket-list worthy? 

Connecticut is a beautiful little state with a lot of wonderful small towns that are so delightful they belong on everyone’s to-do list. Some of the best bucket-worthy small towns in Connecticut are ones like:   

• Washington – If you’re a fan of the classic show Gilmore Girls, you’ll be happy to know the fictional town from the show was inspired by this very real one in Connecticut!   
• Ridgefield – If you’re into artsy things, this is the town for you, featuring plenty of wonderful galleries, eateries, and shops.   
• Putnam – This is the epitome of a foodie town; you’ll find plenty of places to eat here that you’ll never find anywhere else.   

Learn more about these amazingly wonderful bucket-list towns in Connecticut .    

• What are some of the best small towns in Connecticut for families? 

Of course, every small town is lovely – but some are extra perfect for families with kids! Some of the best small towns in Connecticut for families are:   

• Old Greenwich – This area is known for its A+ schools, parks, and overall family-friendly vibe.  
• Riverside – Another area with excellent schools, Riverside is perfect for families with just one or multiple little ones.   
• Ridgefield – We know, we mentioned this one already – but it’s so perfect it’s worth mentioning again thanks to its parks and rec.   

Learn more about some of our other favorite small towns in Connecticut .  

• What are some cool things to do in Connecticut? 

Connecticut might be a state on the smaller side, but there’s plenty to do here! There are so many wonderful things to do in Connecticut that we simply can’t list them all, but some of our favorites include:   

• Visit any (or all) of our amazing state parks – with more than 130 amazing state park sites to choose from, you could make a lifetime out of exploring every one.   
• Go on a road trip – there are so many options here! From foodie road trips to small towns, ghost towns, and restaurants, you never know what kind of adventures you can piece together.   
• Go hiking – Connecticut is home to some of the most beautiful hiking trails in the world.   

Learn more about all these awesome ideas for cool things to do in Connecticut !    

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• 13 Best Small Towns To Visit In Connecticut

Connecticut , a state in the scenic northeastern United States, entices visitors with its subtle beauty and enduring fascination. The rich heritage of Connecticut, sometimes known as the "Constitution State," is evident in its cobblestone streets and historic sites. While people easily overlook this tiny state amidst its larger and bustling neighbors, it holds many enchanting small towns. These quaint retreats perfectly capture the essence of New England, where picturesque surroundings and historical buildings combine to create an explosion of visual delight. Entering these small villages is like walking into a postcard where time stands still with a strong sense of community.

The Connecticut town of Mystic is an intriguing location skillfully combining culture, history, and maritime charm along the peaceful Mystic River shores. Tour the Mystic Seaport Museum, the country's top maritime museum, and travel back to the past as one learns about historic vessels, engaging displays, and fascinating demonstrations. Travelers can walk through the town's lovely streets dotted with adorable shops, galleries, and mouthwatering seafood restaurants. Make sure to try the exquisite Mystic pizza, a regional delicacy gaining attention on a global scale. Visitors can take a lovely boat trip down the Mystic River, inhale the salty air, and take in the breathtaking scenery all around them. Mystic radiates beauty around every corner, promising an unforgettable experience. 

The picturesque village of Essex, nestled on the Connecticut River shores, entices visitors with its enduring beauty and quaint-town appeal. The cozy New England treasure is a fantastic vacation spot for history enthusiasts and architecture lovers with its rich past, appearing in its meticulously-maintained colonial-style buildings and delightful village center. The Connecticut River Museum is a must-visit, offering a fascinating glimpse into the region's maritime past. On the Essex Steam, enjoy a leisurely trip down the Connecticut River. Visit the town's art studios and galleries to learn more about regional artisans and their skills, or admire a show at the iconic Ivoryton Playhouse, a historic theatre regularly presenting theatrical productions. Essex is a mesmerizing location beckoning tourists to take their time, lose themselves in its appeal, and make priceless memories in a town that looks like a real-life postcard.

Cornwall, a quintessential Connecticut small town set in the gently rolling landscape of Litchfield County, is a destination for people looking for a calm escape amidst breathtaking natural beauty, renowned for its stunning surroundings and close-knit population. In Cornwall, travelers can unwind in the serenity of the countryside while taking in the clean air and calming melodies of nature. Kayakers and fishing lovers find solace in the serene waters of the Housatonic River. While outdoor enthusiasts can enjoy winter sports and hiking in the Mohawk Mountain region. Cornwall is a destination where time passes more slowly, allowing tourists to relax, re-establish contact with nature, and appreciate life's simplest pleasures.

Chester, Connecticut, is a must-visit location for visitors looking for a traditional New England encounter featuring its beautifully preserved colonial-era architecture, tree-lined avenues, and buzzing arts scene. Chester's picturesque surroundings would charm nature enthusiasts. The town is hidden in the Connecticut River Valley, encircled by meandering rivers, lush woodlands, and rolling hills. The destination is bursting with creativity, with local artists showing their skills in everything from pottery and painting to sculpture and jewelry. Travelers can discover the Chester Village Historic District, where the streets are lined with houses from the colonial period, taking them back in time. For all the right reasons, Chester is one of Connecticut's best small towns to visit.

The modest town of Kent, nestled amid Connecticut's scenic Litchfield Hills, is a refuge for nature admirers and art lovers. Bounded by undulating hills and unspoiled surroundings, Kent provides a peaceful getaway from the hustle and bustle of daily life. Travelers can explore the town's thriving arts sector, where attractive galleries promise diverse artistic expressions. Visitors can explore the natural beauty of Kent by hiking along the Kent Falls State Park or enjoying a leisurely kayak trip on the Housatonic River. The town center boasts charming stores, friendly cafes, and farm-to-table restaurants beckoning tourists to revel in regional specialties and cute findings. In the middle of New England, tourists can find peace in Kent.

Old Saybrook

Set along the lovely Connecticut coastline. Old Saybrook is a quaint coastal village offering an enticing fusion of heritage, scenic splendor, and coastal beauty. The town is rich in colonial past and is home to several exquisitely-maintained historic landmarks, notably the Lynde Point Lighthouse. Boutique stores, art galleries, and mouthwatering seafood restaurants surround the town's lively Main Street, offering countless choices for shopping and gourmet experiences. Travelers can discover Old Saybrook's serene sandy beaches and beautiful nature paths, making it a refuge for outdoor enthusiasts. Visitors can attend a play at the Katharine Hepburn Cultural Arts Centre or indulge in musical performances at one of the waterfront locations for an evening of artistic endeavors. Old Saybrook promises visitors an unforgettable coastal experience.

Located on Connecticut's stunning Gold Coast, Westport is a charming seaside town effortlessly mixing idyllic scenery with a thriving arts culture. Westport provides a peaceful retreat for beach lovers and water sports enthusiasts with its beautiful marinas, scenic riverfront parks, and immaculate beaches. The town's attractive core is a center of creativity, with theatres, art galleries, and shops showing the creations of regional makers and designers. Visitors can tour the Westport Country Playhouse, an acclaimed regional theatre where top-notch productions have been staged for many years. At the town's top eateries, indulge in farm-to-table fare, or peruse the crowded farmers market for fresh, regional products. Westport is a location that offers the ideal fusion of leisure, culture, and seaside beauty.

The town of Litchfield is a classic New England getaway captivating visitors with its vintage elegance and stunning scenery, nestled in the picturesque Litchfield Hills. Travelers can discover the charming village center, where colonial-era buildings and exquisitely restored homes create a mesmerizing ambiance. Tours to the Tapping Reeve House and Law School, the Litchfield History Museum, and the Litchfield County Jail will help visitors learn more about Litchfield's rich past. Tourists can enjoy exploring Topsmead State Forest's miles of pathways meandering through the neighboring hills, providing spectacular views and an opportunity to observe local species. Litchfield enables tourists to travel back in the past to discover the appeal of a typical New England town with its eternal beauty, intriguing history, and tranquil surroundings.

The charming coastal resort of Madison provides the ideal pair of small-town appeal and coastal serenity. Madison welcomes guests to kick back, unwind, and soak the seaside ambiance with its immaculate sandy beaches, lovely downtown area, and inviting population. Travelers can spend time relaxing on the shoreline, swimming in the Long Island Sound, or hiking through Hammonasset Beach State Park's picturesque nature paths. Explore the shops and galleries dotting Madison's Main Street. At waterfront eateries, taste fresh seafood while savoring the flavors of the ocean. Madison is a place that captures the spirit of a traditional New England beachfront town with its coastal scenery, genuine welcome, and laid-back environment.

With its spectacular landscape and charming appeal, the town of Niantic provides a tranquil seaside vacation on the Connecticut coast. Travelers can enjoy a leisurely stroll down the picturesque Main Street, dotted with shops, cafes, and antique stores. Discover the tiny village center with its old buildings and lovely cafés, or learn about the town's nautical background while strolling the Niantic Bay Boardwalk, where visitors can soak in magnificent ocean views. Niantic's sandy beaches are the ideal location for picnicking, swimming, and tanning. Rocky Neck State Park is another go-to spot for swimming adventures and peaceful times by the water's side. Niantic is an invisible seaside gem that guarantees a revitalizing and unique experience.

Greenwich is a place that beautifully brings together natural splendor with modern conveniences and cultural refinement. The community is recognized for its opulent houses, spotless parks, and energetic downtown. Travelers can discover the elegant shops, restaurants, and art galleries that line the lovely Greenwich Avenue. While the Greenwich Audubon Centre provides environmental paths and educational programs for nature lovers, the Bruce Museum features several art and scientific exhibits. For people who value luxury and the best in life, Greenwich offers a lavish getaway with its sumptuous surroundings, cultural attractions, and natural splendor.

The town of Putnam is a quaint and refreshing destination delivering historic elegance with a booming arts and culinary culture. Travelers can discover the town's newly renovated downtown, brimming with one-of-a-kind boutiques, antique stores, and art galleries. Visitors can stop by the Putnam Historical Society and the Gertrude Warner Museum to learn more about Putnam's rich past. Tourists can indulge in a gourmet journey with farm-to-table cooking and locally produced ingredients at any of the town's renowned restaurants. Putnam is renowned for having a thriving arts community that often hosts art fairs, live music events, and theatre shows. Putnam is a well-kept secret where guests are welcome to look around, indulge, and make lifelong memories.

The town of Chaplin , tucked away in Connecticut's picturesque eastern region, provides a tranquil and lovely escape for people wanting a more leisurely way of life. Take a stroll through the trails of the Natchaug State Forest, go fishing in the crystal-clear Chaplin Lakes, or go kayaking along the Natchaug River. The town's rustic appeal and natural beauty offer the ideal setting for outdoor activity and relaxation. Tour to the Chaplin Museum, featuring artifacts and displays that illustrate the town's background, is a great way to learn about Chaplin's rich past. Historic structures are carefully preserved in the beautiful town center, providing a window into the past. Chaplin is a calm hideaway where one can rediscover the ease and serenity of a little New England village.

Connecticut is an unparalleled repository of small-town attractions thanks to its rich legacy and beautiful scenery. The breathtaking beauty and ageless appeal of these undiscovered gems will enthrall visitors. Every town, from Mystic to Essex, Cornwall to Chester, has its own unique charm and warm energy that draws tourists from all over. Connecticut's little towns provide a wide range of activities to fit any palate and desire, whether it's meandering along cobblestone streets, visiting historic buildings, indulging in delectable cuisine, or bathing in the natural splendor surrounding these communities.

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The 10 Best Small Towns In Connecticut For 2024

The best small towns in connecticut are noank and wilton center for 2024 based on saturday night science..

You’ve seen these lists before. Best places to live in Connecticut . Best sururbs in Connecticut. Best counties in Connecticut.

Etc., etc., etc.

But they all focus on major cities and towns in the Constitution State, and no one pays attention to the little guy.

Well, that’s all about to change as we put together a list of the superb small towns in Connecticut based on numbers–not opinions or hearsay.

We’ll dive right into our methodology in the next section, but first, we thought you might want to know which places in Connecticut ranked the best based on Saturday Night Science .

Table Of Contents: Top Ten | Methodology | Summary | Table

The 15 Best Small Towns To Live In Connecticut For 2024

• Wilton Center
• Madison Center
• Old Saybrook Center
• Guilford Center
• West Simsbury
• Essex Village
• Collinsville

What’s the best small town in Connecticut? Noank is the best small town in Connecticut based on the most recent Census data. If you live in one of these small towns like Noank, chances are, you’re not surprised. After all, you know how great you have it.

But for the rest of you–keep reading, and we’ll get to just why these small towns made our list.

For more reading on the Constitution State check out:

• Best Places To Live In Connecticut
• Cheapest Places To Live In Connecticut
• Most Dangerous Cities In Connecticut

The 15 Best Small Towns In Connecticut For 2024

Population: 1,708 Median Income: $156,842 (4th Best) Median Home Value: $559,298 (10th Best) Unemployment Rate: 0.9%

2. Wilton Center

Population: 1,642 Median Income: $130,543 (10th Best) Median Home Value: $578,869 (9th Best) Unemployment Rate: 2.4%

3. Weatogue

Population: 2,671 Median Income: $154,716 (7th Best) Median Home Value: $433,503 (24th Best) Unemployment Rate: 0.7%

4. Glenville

Population: 3,112 Median Income: $197,619 (1st Best) Median Home Value: $1,163,162 (1st Best) Unemployment Rate: 7.4%

5. Woodmont

Population: 1,619 Median Income: $97,171 (26th Best) Median Home Value: $510,447 (16th Best) Unemployment Rate: 2.8%

Population: 4,417 Median Income: $126,854 (13th Best) Median Home Value: $542,439 (12th Best) Unemployment Rate: 3.7%

7. Pemberwick

Population: 3,212 Median Income: $122,546 (14th Best) Median Home Value: $966,393 (3rd Best) Unemployment Rate: 5.4%

8. Madison Center

Population: 1,536 Median Income: $130,625 (9th Best) Median Home Value: $756,538 (5th Best) Unemployment Rate: 2.7%

9. Litchfield

Population: 1,355 Median Income: $121,346 (16th Best) Median Home Value: $471,964 (18th Best) Unemployment Rate: 4.9%

10. Old Saybrook Center

Population: 2,017 Median Income: $79,712 (43rd Best) Median Home Value: $466,986 (19th Best) Unemployment Rate: 0.0%

11. Guilford Center

Population: 2,541 Median Income: $88,850 (33rd Best) Median Home Value: $649,371 (7th Best) Unemployment Rate: 0.6%

12. West Simsbury

Population: 2,796 Median Income: $175,045 (2nd Best) Median Home Value: $539,610 (13th Best) Unemployment Rate: 4.5%

Population: 1,959 Median Income: $144,375 (8th Best) Median Home Value: $532,182 (14th Best) Unemployment Rate: 3.4%

14. Essex Village

Population: 2,725 Median Income: $98,611 (25th Best) Median Home Value: $869,129 (4th Best) Unemployment Rate: 0.0%

15. Collinsville

Population: 3,750 Median Income: $101,336 (23rd Best) Median Home Value: $433,150 (25th Best) Unemployment Rate: 2.2%

Next 10 Cities

Methodology: How We Determined The Coolest Towns In Connecticut

We threw a lot of criteria at this report to get the best, most complete results of the best small towns in Connecticut possible.

Using the most recent data from the Census’s 2018-2022 American Community Survey, the Bureau of Labor Statistics, and Saturday Night Science , this is the criteria we used:

• Population Density (Higher is better)
• Lowest Unemployment Rates
• Housing costs (Higher is better. More demand.)
• Adjusted Median Income (Higher is better)
• Highly Educated Adults (Higher is better)
• Insurance Rates (Higher is better)
• Commute Times (Lower is better)

We looked at places with populations lower than 5,000 people and greater than 1,000, of which there were many – 67 to be exact.

We then ranked each place in each category with scores from 1 to 67, averaged them out, and the lowest scores went to our Best Small Towns in Connecticut. Top of that list — Noank.

This is our tenth time ranking the best small places to live in Connecticut .

Summary: Science Can Tackle Any Issue, Even Small Ones

We said it once, and we’ll say it again — this list: it’s just science. We did the research, crunched the numbers, and it turns out these 15 small towns in Connecticut are the best in which to live.

And who can argue with that?

The best small towns in Connecticut are Noank, Wilton Center, Weatogue, Glenville, Woodmont, Mystic, Pemberwick, Madison Center, Litchfield, and Old Saybrook Center.

If you’re curious, here are the worst small towns in Connecticut:

• North Grosvenor Dale

For more Connecticut reading, check out:

• Best Places To Raise A Family In Connecticut
• Safest Places In Connecticut
• Worst Places To Live In Connecticut

Best Small Towns In Connecticut

Chris Kolmar has been in the real estate business for almost ten years now. He originally worked for Movoto Real Estate as the director of marketing before founding HomeSnacks.

He believes the key to finding the right place to live comes down to looking at the data, reading about things to do, and, most importantly, checking it out yourself before you move.

If you've been looking for a place to live in the past several years, you've probably stumbled upon his writing already.

You can find out more about him on LinkedIn or his website .

Screen Rant

10 places like gilmore girls' stars hollow to visit in real life.

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10 Of Stars Hollow's Quirkiest Celebrations In Gilmore Girls

Gilmore girls: 10 things that make no sense about stars hollow, gilmore girls: 10 things about stars hollow residents that would never fly today.

• Gilmore Girls ' Stars Hollow is an iconic fictional town, but real-life towns like Washington, Connecticut, share its cozy vibes.
• Ligonier, Pennsylvania, with its colonial history and annual Fort Ligonier Days festival, captures the historical charm of Stars Hollow.
• Despite its seaside location, Camden, Maine evokes the same idyllic atmosphere as Stars Hollow, complete with an old-school diner and cafe.

Towns like Stars Hollow in Gilmore Girls are magical places, and the show's small-town feel can be recreated by visiting similar real-life locations. For seven seasons, Gilmore Girls focused on the mother-daughter duo of Lorelai (Lauren Graham) and Rory (Alexis Bledel) as they navigated romantic relationships, school, and careers while residing in the tight-knit town of Stars Hollow, Connecticut. The town was a huge part of the series' charm.

Gilmore Girls has been praised for its cozy vibes, and a large contributor to the show's warm atmosphere is the backdrop of Stars Hollow. Stars Hollow looks like an idyllic town from a storybook , filled with quirky yet lovable characters and iconic locations such as Kim's Antiques and Luke's Diner. Though the filming location for Gilmore Girls was a Warner Bros. lot in Burbank, California, many real-life small towns have similar vibes to the iconic Stars Hollow that fans fell in love with.

Gilmore Girls: 10 Details In Stars Hollow You Never Noticed

The Gilmore girls take viewers on a tour of their beloved town, Stars Hollow. Here are some details behind the town and all its treasures.

10 Washington, Connecticut

A major inspiration for stars hollows' dragonfly inn.

Washington, Connecticut, served as one of the inspirations for Stars Hollow in Gilmore Girls . Gilmore Girls creator Amy Sherman-Palladino and her husband visited this town after her pitch for the series was accepted. The Palladinos stayed at the Mayflower Inn & Spa, which gave way to the idea for the Independence Inn and Lorelai's Dragonfly Inn (via Explore Washington ). Washington sits halfway between Hartford and New Haven, which accurately sums up Stars Hollow's location.

Like Stars Hollow, Washington also has colonial architecture, cute shops, and an old-school movie theater.

Both towns share a similar small-town feel with Washington actually being even smaller than Stars Hollow. While Gilmore Girls establishes that Stars Hollow has a population of 10,000, Washington is under 4,000 . Like Stars Hollow, Washington also has colonial architecture, cute shops, and an old-school movie theater. The Palladinos' stay in the town was integral to shaping the identity of Stars Hollow.

9 Ligonier, Pennsylvania

The site of a battle in the french and indian war.

In Gilmore Girls , Stars Hollow is a town filled with history. It was founded by colonial settlers and was the site of the fictional Battle of Stars Hollow, a Revolutionary War conflict that the townspeople reenact in Gilmore Girls season 1, episode 8, "Love and War and Snow." The "battle" was actually said to have included 12 soldiers who were waiting for "redcoats" to arrive only for them to never show up . The quirky piece of history fits the whimsical tone of the show well, but it also helps to connect it to other small towns that have rich backstories.

Ligonier commemorates this key battle with Fort Ligonier Days, a three-day festival.

Like the Gilmore Girls ' setting, Ligonier, Pennsylvania also has a colonial history. This Pennsylvania town was settled in the 1760s (via POPSUGAR ), which is slightly earlier than the founding of Stars Hollow which was in 1779. Ligonier was the site of a battle, however, it was in the French and Indian War rather than the American Revolutionary War like Stars Hollow. Ligonier commemorates this key battle with Fort Ligonier Days, a three-day festival. Much like Stars Hollow, Ligonier also has a beautiful gazebo in one of the local parks.

Gilmore Girls: The 10 Best Stars Hollow Events

Stars Hollow hosts a slew of events for the Gilmore Girls to enjoy. But which festivals are the best? Take a look and see if you agree.

8 Camden, Maine

A town with a café similar to luke's diner.

Stars Hollow is quite picturesque, making for an ideal quaint community that suits the easygoing and charming nature of the series. While such settings tend to only exist in movies and TV shows, the kind of picturesque beauty that Stars Hollow offers can be found in Camden, Maine, a similarly gorgeous town. Camden differs from Gilmore Girls ' famed setting because of its seaside location, but its stunning foliage during autumn gives off similar vibes to Stars Hollow in the fall.

Like Stars Hollow, Camden also contains an old-school diner and café. Stars Hollow has Luke's Diner , where Lorelai and Rory frequently grab a cup of coffee, while Camden is known for Bagel Café, a cozy place that serves all-day breakfast and, of course, coffee. Such small seaside towns also feature charming shops and a nice atmosphere for walking around which appeals to tourists who seek out such places in the warmer summer months.

7 Rockport, Massachusetts

A town like stars hollow filled with quaint shops.

In Gilmore Girls , Rory dreams of attending Harvard , so it's fitting that a Massachusetts town appears on this list. Located on the tip of the Cape Ann Peninsula, Rockport is a charming New England town. According to Rockport USA , a variety of cute shops line Rockport's streets, from the bookstore Susie's Stories to Windmere Art & Antiques. These are similar to Stars Hollow's Black-White-Read bookstore and Kim's Antiques.

Like Stars Hollow, Rockport also has a quaint collection of inns , as well as the Sandy Bay Historical Society and Museums, much like Stars Hollow's Historical Society and Museum seen in the Gilmore Girls season 5 episode "To Live and Let Diorama." It is another small town with a population of less than 7,000. Like Camden, Rockport is a seaside community with a heavy fishing presence. While it might make for a different focus among the citizens, such communities often include the same welcoming population that is seen in Gilmore Girls.

Throughout Gilmore Girls, the inhabitants of Stars Hollow organize plenty of curious and bizarre celebrations that make their town interesting.

6 Friday Harbor, Washington

A town like stars hollow with a coffee experience that rival's luke's diner.

Though New England has plenty of locations that evoke the same feelings as Stars Hollow, it's not the only region that has that small-town magic. Friday Harbor, located on Washington's San Juan Island, is also a great place to visit. As Paste Magazine states, the town has a coffee experience "that rivals even Luke's" at the Crow's Nest Coffee Shoppe.

Friday Harbor has a love of festivals that rivals Stars Hollow's; Town Square Publications mentions a number of festivals, including the Friday Harbor Film Festival. Avid Gilmore Girls fans will be reminded of the Stars Hollow Movie Festival, an annual movie night in the town square. However, it also offers a lot of different aspects with its island location accessible by ferry and seaplane. While Stars Hollow can sometimes feel separated from the rest of the world, those looking to have that isolated and relaxing vibe could find it in a place like Friday Harbor.

5 Sturbridge, Massachusetts

A town like stars hollow that hosts an annual revolutionary war reenactment.

Sturbridge, Massachusetts is a beautiful New England town that is sure to delight Gilmore Girls enthusiasts. Settled in 1729, Sturbridge has a rich colonial history. The town hosts Redcoats and Rebels, an annual Revolutionary War reenactment held in Old Sturbridge Village, a living historical town that recreates life in rural New England — and the event certainly echoes celebrations of The Battle of Stars Hollow reenactment in Gilmore Girls .

Sturbridge also features a stunning gazebo at the Publick House Historic Inn & Country Lodge, as well as Churchill Village Eatery, a cozy restaurant that serves delicious breakfast foods that even Luke Danes would approve of. The Sturbridge Public Library also captures Stars Hollow's small and historic feel. It was established in 1873 and has been maintained with pride and dedication by the town ever since. The nearby Wells State Park is a massive woodland that also gives the locale a closer feel to the cozy autumn feel of Stars Hollow.

As much as fans love the hometown of their favorite Gilmore Girls characters, they can admit that not everything about Stars Hollow makes sense.

4 Kent, Connecticut

Another connecticut town like stars hollow that has a bakery similar to weston's.

Kent, Connecticut is another town Sherman-Palladino and her husband visited during their travels. Kent was settled in 1739, making it another historically significant town, however, it's much smaller than Stars Hollow, with a population of just over 3,000. But similar to the Gilmore Girls town, Kent has a beautiful gazebo on the green and a downtown section filled with cute shops. There's a local bakery, Kent Coffee & Chocolate, that will remind Gilmore Girls fans of Weston's Bakery.

Alex Borstein, who famous voices Lois Griffin in Seth Macfarlane's Family Guy was originally supposed to play Sookie. However, Borstein did play both Drella the harpist and Miss Celine in Gilmore Girls .

A post from the travel blog Planned Wanderings describes The Villager Restaurant, an eatery that serves American and Mexican food , as " if Al's Pancake World and Luke's Diner had a baby. " Kent also has a number of antique shops. One in particular — Lyme Regis Ltd — gives off a Kim's Antiques vibe. As a fun bit of trivia related to the town, Kent is also the hometown of Seth MacFarlane. Though MacFarlane is best known for creating Family Guy and the movie Ted , he also played Zach in the Gilmore Girls episode "Lorelai's Graduation Day."

3 New Milford, Connecticut

Another town that influenced amy sherman-palladino when creating stars hollow.

New Milford was another stop on the Palladinos' tour of Connecticut and it is located in Litchfield County, just as Kent is . It is clear that this area offered the kind of climate and conditions that would capture the vibe Gilmore Girls was looking for — a quaint town that is charming in any season, from the colorful autumn to the laidback summer to the cozy winter.

There is also a lot of history to it with the town's public school Sarah Noble being named after the daughter of New Milford's founder.

The town boasts an impressive gazebo on the town green. It even rivals the one in Stars Hollow, and it may have served as an inspiration for it. New Milford has other features that are reminiscent of towns like Stars Hollow, such as a local diner and a historical society . New Milford is another example of a charming small Connecticut town, and it's easy to see how Sherman-Palladino was inspired by it, as well as other spots in Litchfield County.

Stars Hollow residents from Gilmore Girls make for a great community, but unfortunately, some of their behaviors haven't aged all that well.

2 Ridgefield, Connecticut

Ridgeport west lane is very similar to the dragonfly inn.

Located an hour and a half from New York City, Ridgeport is another quaint Connecticut town that could not be more different from the big city. According to Suburbs 101 , Ridgeport's West Lane Inn is a designated historical landmark and shares a similar origin story to the Dragonfly Inn in Stars Hollow . The West Lane Inn was built in 1849 and updated its decor in 2020, while the Dragonfly Inn was built in 1893 and renovated by Lorelai and Sookie in Gilmore Girls .

The town also has a local bookstore, Books on the Common, that's as charming as Stars Hollow Books.

The town also has a local bookstore, Books on the Common, that's as charming as Stars Hollow Books, where Rory works in Gilmore Girls season 5. The local history museum also has a similar story to the Stars Hollow History Museum. Stars Hollow's museum was originally the house of resident Joshua Twickham, while Ridgeport's Keeler Tavern Museum was the home of architect Cass Gilbert. The town was also the setting for the Battle of Ridgefield on April 27, 1777, during the American Revolutionary War.

1 New Hope, Pennsylvania

New hope is a perfect substitute for stars hollow.

New Hope, Pennsylvania is a charming town located about an hour's drive from both New York City and Philadelphia. It is one of the smallest towns on this list, boasting just over 2,500 residents as of a 2020 census. New Hope is also another town steeped in the kind of little-known American history that the people of Stars Hollow take such pride in, as it was the town where George Washington stayed the night before his historic crossing of the Delaware River.

Like towns like Stars Hollow, New Hope has a warm and inviting atmosphere, as well as gorgeous fall foliage and charming houses and shops . Paste Magazine mentions the acclaimed Inn at Bowman's Hill, as well as the Blue Moose Restaurant and Café. With its eclectic stores, and the Acme Screening Room, a nearby indie movie theater, New Hope is a perfectly suitable substitute for the town of Stars Hollow in Gilmore Girls .

Gilmore Girls

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In the fictional town of Star's Hollow, single mother Lorelai Gilmore raises her high-achieving teenage daughter Rory. Mother and daughter rely on each other throughout their own life changes, romantic entanglements, and friendships.

America's Best Towns to Visit

10 great US towns to check out now

These destinations, selected by CNN Travel editors, offer loads of personality and plenty to see and do without the elbow-to-elbow crowds of the big tourist cities.

Making the most of life on the lake: How this town got its cool reputation

This ‘scruffy little city’ tastes and sounds great

Why ‘Beer City USA’ is so much more than a drinking town

From ‘ghost town’ to ‘popping’: How this Southern destination got its groove back

This Grand Canyon pit stop is now a bona fide hot spot

The laid-back California dream lives on here

This coastal culinary hub has a ‘big-city feel in a small-city package’

‘Grit City’ shines thanks to stunning scenery and glass art

This Rhode Island gem moved rivers to emerge as New England’s creative capital

Our top town offers first-rate arts, food and festivals and a hard look at its complicated history

how we chose

We tapped our network of CNN Travel contributors for nominations for our inaugural list, winnowing the finalists to 10 by looking at each town's attractions, food and beverage offerings, nightlife and cultural scene, sense of identity, proximity to other interesting spots and wow factor. We also looked at lodging options and the ease of getting there and around.

PHOTO CREDITS

• Intro : Chris Johnson/Visit Richmond
• Duluth : Visit Duluth
• Knoxville : SeanPavonePhoto/iStockphoto/Getty Images
• Grand Rapids : Ideology/Experience Grand Rapids
• Macon : Visit Macon
• Flagstaff : CNN
• San Luis Obispo : Brittany App/Visit SLO
• Portland : Visit Portland
• Tacoma : CNN/Travel Tacoma/Museum of Glass
• Providence : N. Millard/GoProvidence.com
• Richmond : Richmond Region Tourism