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Daytripping Through Maryland’s Eastern Shore: 5 Perfect Day Trips

The hidden gem of Maryland’s Eastern Shore is a treasure trove, providing the perfect day trip destination from many other places on the East Coast. It has a little of everything, catering to every possible interest: natural beauty, historical significance, and loads of seaside, small-town charm.

From the tranquil, wispy sand dune-studded shores of Assateague Island to countless historic destinations holding very literal national treasures and deep secrets, each day trip offers visitors a unique experience. Whether you’re a history buff, an outdoor enthusiast, or even seeking a peaceful family summer vacation , Maryland’s Eastern Shore has plenty to offer.

Immerse in The Great Outdoors at the Assateague Island National Seashore

No trip to the Eastern Shore is complete without a visit to the Assateague Island National Seashore . Known for its free-roaming wild ponies and miles of pristine sand dune-studded beaches , this barrier island offers an unforgettable experience. The seashore sits in both Maryland and Virginia, and each side offers endless adventure.

assateague island ponies

Explore the 37-plus miles of hiking and biking trails, go crabbing for those famous Maryland Blue Crabs, try surf fishing, go birdwatching or horseback riding , kayaking, camp overnight, or relax on the sandy shores. You might spot the famous wild horses grazing along the shoreline if you’re lucky!

Take a Step Back in Time in St. Michaels

St. Michaels is the epitome of a waterfront East Coast town, with beautiful scenery, charming streets lined with local restaurants and boutiques, and an atmosphere that’s both laid-back and bustling.

One of the town’s main attractions is the renowned Chesapeake Bay Maritime Museum , where visitors can immerse themselves in the area’s rich maritime history as they explore the exhibits. These include a marina full of historic boats, interactive displays, and the Hooper Strait Lighthouse (circa 1879). The museum even offers scenic river cruises aboard its 1920 boat, Winnie Estelle .

Hooper Strait Lighthouse

There are several other ways to explore the river outside the museum’s offerings, including narrated sunset tours and sailing charters. Prefer to do the navigating yourself? Go kayaking, stand up paddleboarding or canoeing!

This quaint seaside town also has excellent shopping, dining, wineries, and breweries. Some highlights include St. Michaels Winery and Eastern Shore Brewing, both award-winning establishments with great tasting rooms. Crab Claw is also a can’t-miss, a family-owned seafood restaurant on a dock overlooking the river.

Explore Historic Tilghman Island

Just 11 miles west of St. Michaels, separated from the mainland but connected via a drawbridge, Tilghman Island makes another beautiful day trip on Maryland’s Eastern Shore.

This scenic fishing village is known for its natural beauty , abundant boating opportunities, and some of the best seafood on the Eastern Seaboard. Particularly, Tilghman Island has long-standing roots in the oyster industry, which offers excellent dining and tour options.

Don’t leave town without checking out Rebecca T. Ruark , the oldest skipjack boat on the Chesapeake Bay! The boat was built in 1896 and earned an official National Historic Landmark designation in 2003.

Discover Kent Island’s Arts Scene (and a Hidden Beach!)

Kent Island is the biggest island in the Chesapeake Bay, the major link between Maryland’s western and eastern shores. There’s plenty to see and do here, making it one of the best options. The quaint, historic town of Stevensville is a wonderful place to start, offering a little something for every type of day-tripper. 

Start in the Arts & Entertainment District, and if you can time it right, aim for a Saturday. On the first Saturday of every month from April through December, the district hosts First Saturday events , which include a local farmers’ market and open house-style tours of many of the area’s historical sites and homes. There are also plenty of antique shops, art galleries, and great cafes in the arts district, so it’s easy to fill an entire day without venturing very far.

sunset in kent island maryland

Music enthusiasts won’t want to miss touring the Paul Reed Smith (PRS) guitar factory in town. The top-of-the-line facility is a sight to behold in its own right, but visitors can also try their hand — literally — at playing world-class guitars and witness them being made in live time. Prominent musicians like Carlos Santana and Dave Navarro of Red Hot Chili Peppers and Jane’s Addiction have their guitars made here!

One of the main reasons to visit Kent Park is its outdoor attractions. Head to the Terrapin Nature Park , with picnic areas, great hiking trails, and a “hidden” beach overlooking the Bay Bridge. Reach it by taking the park’s 3.25-mile main hiking trail. 

Learn About History & the “Everglades of the North” in Cambridge

The Eastern Shore town of Cambridge, about an hour’s drive from Annapolis , has a bit of everything, making it an ideal day trip destination. The Blackwater National Wildlife Refuge, affectionately known as the “Everglades of the North,” is a great place to start, with miles of biking and hiking trails, great fishing, fascinating marshes, and unbeatable birdwatching opportunities. Stroll through the refuge on your own, or join a guided birdwatching tour. 

Near the wildlife refuge is the plantation where famed abolitionist Harriet Tubman made her final escape from slavery. She would return to the area many times over the years, helping 70 others escape enslavement via the Underground Railroad. Today, you can visit the Harriet Tubman Underground Railroad National Historical Park , where you can walk and drive in the same place she once did, retracing her steps. 

Uncover Maryland’s Eastern Shore

Maryland’s Eastern Shore offers an enchanting journey through a region brimming with natural beauty and delightful experiences. From the picturesque waterfront towns and charming historical sites to the idyllic landscapes and mouthwatering seafood, this coastal paradise has something for every traveler.

Any day trip through Maryland’s Eastern Shore promises to be an unforgettable adventure. Embark on a journey to this captivating region, and prepare to be swept away by the allure of it all.

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The Top 14 Things to Do on Maryland's Eastern Shore

day trips maryland eastern shore

WilliamSherman / Getty Images

The Maryland Eastern Shore , a peninsula extending hundreds of miles between the Chesapeake Bay and the Atlantic Ocean, offers endless recreational opportunities and is a popular summer vacation destination. Visitors from around the region flock to the Eastern Shore to explore its historic towns, beaches, and beautiful natural areas. Visitors can enjoy an array of activities, such as boating, swimming, fishing, bird watching, biking, and golfing. The resort communities along the Eastern Shore host wonderful annual events, including waterfront festivals, seafood festivals, boating regattas and races, fishing tournaments, boat shows, museum events, arts and crafts shows, and more. This guide highlights the best things to do along the Eastern Shore, from hitting the beach to catching a baseball game. Have fun exploring this beautiful part of Maryland.

See the Boats in Chesapeake City

AppalachianViews / Getty Images

The charming small town, located at the northern end of the Eastern Shore, is known for its unique views of ocean-going vessels. The historic area sits just south of the Chesapeake & Delaware Canal, a 14-mile canal that dates back to 1829. The C&D Canal Museum provides a glimpse of the history of the canal for those interested in diving into its rich history.

Visitors can also enjoy art galleries, antique shopping, outdoor concerts, boat tours, horse farm tours, and seasonal events. There are several excellent restaurants and bed-and-breakfasts nearby.

Explore the History of Chestertown

bpalmer / Getty Images 

The historic town on the banks of the Chester River was an important port of entry for early settlers to Maryland. There are many restored colonial homes, churches, and several interesting shops. The Schooner Sultana provides opportunities for students and adult groups to sail and learn about the history and environment of the Chesapeake Bay. Monument Park is a Civil War trail site where you can stroll amongst monuments from the war period. Chestertown is also home to Washington College, the tenth oldest college in the United States.

Boat in One of the Many Marinas in Rock Hall

 Coastal Pics/Getty Images

This quaint fishing town on the Eastern Shore has 15 marinas, making it a favorite stop for boaters. There are a variety of restaurants and shops in town for those passing through, as well as several things to do even when you're not on the water. The Waterman's Museum features exhibits on crabbing, oystering, and fishing. Eastern Neck National Wildlife Refuge is home to 234 species of birds, including nesting bald eagles, and includes amenities such as hiking trails, an observation tower, picnic tables, public fishing areas, and a boat launch.

Enjoy Delicious Seafood and Drinks on Kent Island

L. Toshio Kishiyama / Getty Images

Known as “Maryland’s Gateway to the Eastern Shore,” Kent Island sits at the base of the Chesapeake Bay Bridge and is a rapidly growing community because of its convenience to the Annapolis/Baltimore-Washington corridor. The area has lots of seafood restaurants, marinas, and outlet stores. You'll definitely want to make a stop in one of the island's distilleries and wineries — Blackwater Distillery offers s Sloop Betty Vodka, which won the brand a gold medal for Best Vodka in Show at the New York Wine & Spirits Competition.

Appreciate the Arts in Easton

 Bob Quinn / Pickering Creek Audubon Center 

Located along Route 50 between Annapolis and Ocean City, Easton is a convenient place to stop to dine or take a walk. The historic town is ranked 8th in the book “100 Best Small Towns in America.” Main attractions include antique shops, an art deco performing arts venue — the Avalon Theater — and the Pickering Creek Audubon Center. If you're in the area in July, you might make it for the Plein Air Easton Art Festival, the largest juried plein air (outdoor) painting competition in the United States. You could also stop by the Academy Art Museum, which boasts an art collection of over 1,400 works.

Head to a Popular Museum In St. Michaels

wbritten / Getty Images

The quaint historic town is a popular destination for boaters with its small town charm and a variety of gift shops, restaurants, inns, and bed and breakfasts. The main attraction here is the Chesapeake Bay Maritime Museum , an 18-acre waterfront museum that displays Chesapeake Bay artifacts and features programs about maritime history and culture. The museum has nine buildings and includes an extensive collection of sail, power, and rowboats. St. Michaels is one of the best Eastern Shore destinations for sailing, bicycling, and eating freshly-caught crabs and oysters.

Go Sports Fishing on Tilghman Island

R H Productions / robertharding/Getty Images 

Located on the Chesapeake Bay and the Choptank River, Tilghman Island is known most for sports fishing and fresh seafood. The island is accessible by a drawbridge and has several marinas including a few that offer charter cruises. It is home to the Chesapeake Bay Skipjacks, the only commercial sailing fleet in North America. The island is also perfect for those who enjoy nature — rent a bike, charter a boat (for more fishing), or even rent a kayak or paddleboard.

Step Back in Time in Oxford

coastalpics / Getty Images

This quiet town is the oldest on the Eastern Shore, having served as a port of entry for British trade vessels during Colonial times. Oxford is most well-known for its nautical scene, as there are several marinas in the area. However, the small town has more to offer than just boating. It's a colonial-era town that's home to some beautiful historic markers, such as the Robert Morris Inn, one of the oldest Inns in America, and the 339-year-old Oxford-Bellevue Ferry.

Birdwatch in Cambridge

dmadig / Getty Images 

The main attraction in Cambridge is the Blackwater National Wildlife Refuge, a 27,000-acre resting and feeding area for migrating waterfowl and home to 250 species of birds, 35 species of reptiles and amphibians, 165 species of threatened and endangered plants, and numerous mammals. If you're looking to stay in luxury, the Hyatt Regency Resort, Spa, and Marina, one of the region’s most romantic getaway destinations, sits right on the Chesapeake Bay and has its own isolated beach, an 18-hole championship golf course, and 150-slip marina.

Catch a Baseball Game in Salisbury

Edwin Remsberg / Getty Images 

Salisbury is the largest city on the Eastern Shore with approximately 24,000 residents. Stop in and enjoy a game at the Arthur W. Perdue Stadium, home to the minor-league Delmarva Shorebirds. Don't forget to visit the Eastern Shore Baseball Hall of Fame to see some baseball legends, like Frank "Home Run" Baker. After your game, check out the Salisbury Zoological Park, and the Ward Museum of Wildfowl Art, a museum housing the most extensive collection of bird carvings in the world.

Hit the Beach in Ocean City

Chris Parypa / Getty Images 

With 10 miles of white sand beaches along the Atlantic Ocean, Ocean City, Maryland is the ideal place for swimming, surfing, kite flying, sand castle building, jogging, etc. The Eastern Shore resort is a bustling beach town with amusement parks, arcades, miniature golf courses, shopping malls, an Outlet shopping center, movie theaters, go-kart tracks, and the famous 3-mile Ocean City Boardwalk. There is a wide range of accommodations, restaurants, and nightclubs to appeal to a variety of vacationers.

Spot Wild Ponies at Assateague Island National Seashore

Trina Dopp Photography / Getty Images

Assateague Island is most known for the more than 300 wild ponies who wander the beaches. Since this is a national park, camping is allowed, but you’ll have to drive to nearby Ocean City, Maryland or Chincoteague Island, Virginia to find hotel accommodations. This is a great Eastern Shore destination for bird watching, seashell collecting, clamming, swimming, surf fishing, beach hiking, and more.

Eat Blue Crab in Crisfield

Crisfield is located at the southern end of the Maryland Eastern Shore at the mouth of the Little Annemessex River. Crisfield is home to many seafood restaurants, the annual National Hard Crab Derby, and the Somers Cove Marina, one of the largest marinas on the East Coast. Dubbed "The Crab Capital of the World," you don't want to leave Crisfield without enjoying its delicious blue crab. The area is also perfect for nature lovers — there are plenty of trails for walking and biking.

Take the Ferry to Smith Island

Betty Wiley / Getty Images

Maryland's only inhabited off-shore island on the Chesapeake Bay is accessible by ferry only, from Point Lookout or Crisfield. It's a small island, with only about 200 permanent residents. The island is an interesting piece of remaining colonial history — it's so isolated that residents speak a dialect of English more similar to that which was used during the 17th century. Some describe it as "Elizabethan." It's also the birthplace of Maryland's state dessert, the Smith Island Cake. This is a unique getaway destination with a few bed and breakfasts, the Smith Island Museum, and a small marina.

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59 Best and Fun Things To Do In The Eastern Shore, Maryland

day trips maryland eastern shore

Maryland’s Eastern Shore is a unique and remarkable American destination. With its abundance of charming farmlands, meandering rivers, and welcoming coastal towns, tourists will discover that the Eastern Shore has plenty to explore.

Wild horses roam the pristine beaches of Assateague Island National Seashore and State Park, while eagles soar over the primeval forests of Blackwater National Wildlife Refuge. Ocean City is one of the region’s main attractions, drawing thousands of visitors from all over the country each year.

The Eastern Shore is also recognized as the birthplace of Harriet Tubman and Frederick Douglass, two notable figures in American history who fought against slavery. This makes it an ideal location for lovers of history to learn more about what makes Maryland so special.

Read on for our list of the best and most fun things to do in Eastern Shore, Maryland

The 59 Most Popular Things To Do In The Eastern Shore, Maryland

59. piney island.

4.0 ★★★★☆  (1 review)

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Credit:   Sarah Stierch , License , Flickr

58. Holly Bluff Island

5.0 ★★★★★  (1 review)

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Credit: Brandon, Google Maps

57. Parramore Island

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Credit: Bert Clements, Google Maps

56. Snead Beach

1.0 ★☆☆☆☆  (1 review)

55. Swan Cove Trail

Location: Swan Cove Trail Chincoteague VA

Web Address:   https://npplan.com/parks-by-state/maryland-national-parks/assateague-island-national-seashore-park-at-a-glance/assateague-island-national-seashore-hiking-trails/assateague-island-national-seashore-virginia-hiking-trails/assateague-island-national-seashore-swan-cove-trail/

54. Fishermans Island

5.0 ★★★★★  (2 reviews)

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Credit:   Chesapeake Bay Program , License , Flickr

53. Myrtle Island Beach

3.0 ★★★☆☆  (2 reviews)

52. Cape Charles Lighthouse

4.3 ★★★★☆  (3 reviews)

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Credit: Will Cline, Google Maps

Location: Cape Charles VA

51. Chincoteague Beach

4.8 ★★★★★  (4 reviews)

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Credit:   Ken Lund , License , Wikimedia commons

Location: 8274 Beach Access Road Chincoteague VA

50. Cedar Island Beach

4.0 ★★★★☆  (4 reviews)

49. Kiptopeke Beach

4.9 ★★★★★  (10 reviews)

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Credit: Josh Canulli, Google Maps

48. Makemie Monument Park

4.5 ★★★★★  (10 reviews)

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Credit: Robert Ziegenfus, Google Maps

Location: 699 Temperanceville VA

47. Toms Cove

5.0 ★★★★★  (11 reviews)

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46. Fisherman Island National Wildlife Refuge

4.7 ★★★★★  (12 reviews)

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Web Address:   http://fws.gov/northeast/easternshore/

45. Guard Shore

4.2 ★★★★☆  (12 reviews)

44. Parkers Marsh Natural Area Preserve

3.7 ★★★★☆  (12 reviews)

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Credit: Stephen Thayer, Google Maps

Location: Onancock VA

Web Address:   http://marineprotectedareas.noaa.gov/

43. Saxis Island

4.7 ★★★★★  (13 reviews)

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Credit: Ashley Terry, Google Maps

42. Wreck Island Natural Area Preserve

4.4 ★★★★☆  (16 reviews)

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Credit: Sławomir Prus, Google Maps

Web Address:   https://dcr.virginia.gov/natural-heritage/natural-area-preserves/wreck

41. Spider’s Explorer

5.0 ★★★★★  (16 reviews)

Af1qippxn4dl-7b7ytrvo4x-djdu-lfuidkgswvwizwu=w592-h404-n-k-no

Credit: Samson Stevens Sr., Google Maps

Location: 3801 South Main St Chincoteague VA

Tel:   757 990 4242

Web Address:   http://chincoteaguespider.com/

40. Magothy Bay State Natural Area Preserve

4.2 ★★★★☆  (18 reviews)

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Credit: Jen Barnes, Google Maps

Location: 35540 Kiptopeke Dr Cape Charles VA

Tel:   757 787 5576

Web Address:   https://dcr.virginia.gov/natural-heritage/natural-area-preserves/magothybay

39. Saxis Island Museum & Old Crockett Store

4.9 ★★★★★  (19 reviews)

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Credit: Saxis Island Museum & Old Crockett Store, Google Maps

Location: 20101 Saxis Road Saxis VA

Tel:   410 948 0555

Web Address:   http://saxisislandmuseum.org/

38. Bivalve Trail

4.4 ★★★★☆  (28 reviews)

Af1qipp9cjfy9atgr4nhjve4abrt0bohj74j8u 2cf1n=w592-h404-n-k-no

Credit: Malissa Yocum, Google Maps

Location: Woodland Trail Chincoteague VA

Web Address:   https://npplan.com/parks-by-state/maryland-national-parks/assateague-island-national-seashore-park-at-a-glance/assateague-island-national-seashore-hiking-trails/assateague-island-national-seashore-virginia-hiking-trails/assateague-island-national-seashore-bivalve-trail/

37. Public Beach of Tangier Island

4.6 ★★★★★  (31 reviews)

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Credit: Wayne Leone, Google Maps

36. Savage Neck Dunes Natural Area Preserve

4.8 ★★★★★  (32 reviews)

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Credit: Patrick Kerr, Google Maps

Web Address:   http://dcr.virginia.gov/natural_heritage/natural_area_preserves/savage.shtml

35. Lemon Tree Gallery and Studio

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Credit: Lemon Tree Gallery and Studio, Google Maps

Location: 301 Mason Ave #3203 Cape Charles VA

Tel:   757 331 4327

Web Address:   http://lemontree.gallery/

34. Eastern Shore of Virginia Historical Society-Ker Place

4.9 ★★★★★  (33 reviews)

Af1qipmrsyluog6b7yvqc4rgceaphaoc0pch7cc17alr=w592-h404-n-k-no

Credit: Eastern Shore of Virginia Historical Society/Ker Place, Google Maps

Location: 69 Market Street Onancock VA

Tel:   757 787 8012

Web Address:   http://shorehistory.org/

33. Mutton Hunk Fen State Natural Area Preserve

4.4 ★★★★☆  (34 reviews)

Af1qipn6c2wuhr3qdajlflydywk0f1z61ftbobcb3odq=w592-h404-n-k-no

Credit: Grey Cat, Google Maps

Location: 28583 Baker Road Parksley VA

Web Address:   https://dcr.virginia.gov/natural-heritage/natural-area-preserves/muttonhunk

32. Brownsville Preserve – Virginia Coast Reserve

4.8 ★★★★★  (37 reviews)

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Credit: Carrie Dellesky, Google Maps

Location: 11332 Brownsville Road Nassawadox VA

Tel:   757 442 3049

Web Address:   http://nature.org/vcr

31. Virginia Hang Gliding

4.9 ★★★★★  (38 reviews)

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Credit: Virginia Hang Gliding, Google Maps

Location: 16620 Coal Kiln Road Painter VA

Tel:   757 346 1134

Web Address:   http://virginiahanggliding.info/

30. Chincoteague Bay Field Station

4.7 ★★★★★  (58 reviews)

Location: 34001 Mill Dam Road Wallops Island VA

Tel:   757 824 5636

Web Address:   http://cbfieldstation.org/

29. Eyre Hall

4.8 ★★★★★  (60 reviews)

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Credit: Douglas W. Reynolds, Jr., Google Maps

Location: 3215 Eyre Hall Drive Cheriton VA

Web Address:   https://co.northampton.va.us/visitors/tourism/free_things_to_see_and_do/free_history_lessons/eyre_hall_gardens

28. Tomb of Custis

4.2 ★★★★☆  (62 reviews)

Af1qipoifnhvjj6xx6fxakucjgpjp4q5m-oixalkepsc=w592-h404-n-k-no

Credit: William Stubbs, Google Maps

Location: 2157 Arlington Chase Road Cape Charles VA

27. Chincoteague Island Waterman’s Memorial

4.8 ★★★★★  (65 reviews)

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Credit: Jaime Rutherford, Google Maps

Location: Chincoteague VA

Web Address:   https://facebook.com/watermansproject

26. Cape Charles Natural Area Preserve

4.5 ★★★★★  (68 reviews)

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Credit: TJ Colaci, Google Maps

Web Address:   http://dcr.virginia.gov/natural_heritage/natural_area_preserves/capecharles.shtml

25. Island Nature Trail

4.6 ★★★★★  (71 reviews)

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Location: Hallie Whealton Smith Dr Chincoteague VA

Tel:   757 336 6519

Web Address:   https://chincoteague-va.gov/citizens/recreation

24. Indiantown Park

4.7 ★★★★★  (75 reviews)

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Credit: Cody Waldron, Google Maps

Location: 7399 ntown Road Eastville VA

Tel:   757 678 0468

Web Address:   https://dwr.virginia.gov/vbwt/sites/indiantown-park/

23. Captain Timothy Hill House

4.7 ★★★★★  (90 reviews)

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Credit: Captain Timothy Hill House, Google Maps

Location: 5122 Main Street Chincoteague VA

Tel:   914 589 7733

Web Address:   http://captaintimothyhillhouse.com/Home.html

22. Chincoteague Island

4.8 ★★★★★  (93 reviews)

21. Saxis Wildlife Management Area

4.5 ★★★★★  (95 reviews)

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Credit: Sara Sullivan, Google Maps

Location: Bloxom VA

Web Address:   https://dgif.virginia.gov/wma/saxis/

20. Tangier History Museum

4.6 ★★★★★  (101 reviews)

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Credit: RJ Whaley, Google Maps

Location: 16215 Main Ridge Road Tangier VA

Tel:   757 891 2374

19. Cape Charles Fishing Pier

4.7 ★★★★★  (140 reviews)

Location: 21 Bay Ave Cape Charles VA

Web Address:   https://mrc.virginia.gov/vsrfdf/capecharles.shtm

18. Cape Charles Museum & Welcome

4.5 ★★★★★  (141 reviews)

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Credit: Jeff Wilson, Google Maps

Location: 814 Randolph Ave Cape Charles VA

Tel:   757 331 1008

Web Address:   https://capecharlesmuseum.org/

17. Cape Charles Historic District

4.6 ★★★★★  (152 reviews)

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Credit: Maria Patricia Roldan-Hernandez, Google Maps

Location: 5 T 1115 Cape Charles VA

Web Address:   http://capecharles.org/pView.aspx

16. Funland Amusements

4.4 ★★★★☆  (161 reviews)

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Credit: Angela J, Google Maps

Location: 6528 Maddox Blvd Chincoteague VA

Tel:   757 336 5420

Web Address:   http://gotofunland.com/

15. Eastern Shore Railway Museum

4.5 ★★★★★  (183 reviews)

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Credit: Paul Reier, Google Maps

Location: 18468 Dunne Ave Parksley VA

Tel:   757 665 7245

14. Barrier Islands Center

4.8 ★★★★★  (185 reviews)

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Credit:   vastateparksstaff , License , Wikimedia commons

Location: 7295 Young Street Machipongo VA

Tel:   757 678 5550

Web Address:   https://barrierislandscenter.org/

13. Savage Neck Dunes State Natural Area Preserve Parking Lot

4.8 ★★★★★  (191 reviews)

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Credit: shuslig83, Google Maps

Location: 2186 Savage Neck Road Drive Cape Charles VA

Tel:   757 787 5989

12. Poseidon Watersports Jet Ski Rental

5.0 ★★★★★  (232 reviews)

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Credit: Poseidon Watersports Jet Ski Rental, Google Maps

Location: 11 Marina Road Cape Charles VA

Tel:   757 902 0400

Web Address:   http://poseidonwatersportsva.com/

11. Museum of Chincoteague Island

4.7 ★★★★★  (372 reviews)

 alt=

Credit: G. Funk, Google Maps

Location: 7125 Maddox Blvd Chincoteague VA

Tel:   757 336 6117

Web Address:   http://chincoteaguemuseum.com/

10. Veterans Memorial Park

4.6 ★★★★★  (505 reviews)

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Credit: Dr. Chris Ford, Ph.D., Google Maps

Location: 7470 Memorial Park Dr Chincoteague VA

Web Address:   http://chincoteague-va.gov/

9. Assateague Island National Seashore

4.8 ★★★★★  (8,568 reviews)

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Location: 7206 National Seashore Ln Berlin MD

Tel:   443 614 3547

Web Address:   http://nps.gov/asis

Our Top picks

8. tangier island, 7. chatham vineyards & winery.

4.9 ★★★★★  (121 reviews)

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Credit: Chatham Vineyards & Winery, Google Maps

Location: 9232 Chatham Road Machipongo VA

Tel:   757 678 5588

Web Address:   http://chathamvineyards.com/

6. Bay Creek

4.6 ★★★★★  (222 reviews)

 alt=

Credit:   Jstuby , License , Wikimedia commons

Location: 1 Clubhouse Way Cape Charles VA

Tel:   757 331 8620

Web Address:   http://baycreeklife.com/

5. Maui Jack’s Waterpark

4.4 ★★★★☆  (286 reviews)

Location: 6742 Maddox Blvd Chincoteague VA

Tel:   757 336 1800

Web Address:   https://mauijacks.com/

4. Assateague Beach

4.8 ★★★★★  (333 reviews)

3. Assateague Lighthouse

4.7 ★★★★★  (363 reviews)

Location: Assateague Island National Seashore Chincoteague VA

Tel:   757 336 3696

Web Address:   https://assateagueisland.com/lighthouse/lighthouse_info.htm

2. NASA Wallops Flight Facility Visitor Center

4.6 ★★★★★  (1,164 reviews)

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Credit:   NASA Goddard Space Flight Center , License , Flickr

Location: Building J20 Route 175 Chincoteague Road Wallops Island VA

Tel:   757 824 1404

Web Address:   https://nasa.gov/centers/wallops/visitorcenter

1. Chincoteague National Wildlife Refuge

4.8 ★★★★★  (2,997 reviews)

Location: 8231 Beach Road Chincoteague VA

Tel:   757 336 6122

Web Address:   https://fws.gov/refuge/chincoteague/

Final Words:

Thank you for reading our list of the best things to do in The Eastern Shore, Maryland! We hope it helped you plan the perfect itinerary for your next trip to this fantastic destination. Happy travels!

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day trips maryland eastern shore

Day Trip to St. Michael’s on Maryland’s Eastern Shore

Enjoy these beautiful sunsets and sailing adventures on a day trip to St. Michaels on the Eastern Shore of Maryland

If your summer plans don’t already include a day trip to the charming town of St. Michael’s on Maryland’s Eastern Shore, it’s about time you planned one. Our Bed and Breakfast on Maryland’s Eastern Shore is the perfect place to escape this summer, especially if you need a bit of solitude and zen-like relaxation. We wouldn’t blame you if all you wanted to do while here is sit back with a good book and relax, but we’d be remiss not to mention all the great things to do on the Eastern Shore, including taking a day trip to the charming town of St. Michael’s.

St. Michael’s is a picturesque harbor town located approximately an hour south of our Rock Hall Bed and Breakfast. USA Today named it one of the top 10 coastal towns in America, so you can count on it being more than worth the drive to spend the day here. Once you’ve had this fill of St. Michael’s, the comfortable accommodations at our Eastern Shore Bed and Breakfast will be waiting for you. Book your room today!

Day Trip to St. Michael’s, Maryland

Though there is more than enough to do in Rock Hall and the surrounding Chesapeake Bay, it’s sometimes fun to get out and explore. A day trip to St. Michael’s on Maryland’s Eastern Shore is a perfect choice! St. Michael’s is a charming town on Maryland’s Eastern Shore, filled with a delightful combination of bustling marinas, delicious restaurants, and one-of-a-kind boutiques. St. Michael’s is also home to the excellent Chesapeake Bay Maritime Museum, which is a great place to learn even more about the history and life on Maryland’s Eastern Shore.

Like many towns on Maryland’s Eastern Shore, St. Michael’s has a lengthy and fascinating history that dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. Today, there are plenty of wonderful things to do in St. Michael’s, centered around its historic square, St. Mary’s Square, and its bustling harbors. Here’s a roundup of eight of our favorite things to do in St. Michael’s on Maryland’s Eastern Shore:

  • Get established in the town by taking a self-guided walking tour of St. Michael’s on Maryland’s Eastern Shore.
  • Take historic narrated cruises through St. Michael’s Harbor, or charter a boat and enjoy a sailing excursion in The Chesapeake Bay. You can even combine wine tasting with a sailing adventure in St. Michael’s!
  • Enjoy some unique shopping in downtown St. Michael’s , where you’ll find a diverse range of shops and art galleries to browse.
  • Rent a kayak, SUP, or bike from Shore Pedal and Paddle , and enjoy a day exploring St. Michael’s on Maryland’s Eastern Shore, just as you would beautiful Rock Hall, MD.
  • Visit the Chesapeake Bay Maritime Museum and learn all about the history of this unique part of the world.
  • Sometimes, there’s nothing better than relaxing with a cold pint of locally crafted beer on a hot summer day. You’ll find some delicious craft brews at Eastern Shore Brewing in St. Michael’s.
  • Plan to attend at least one of the fun festivals in St. Michael’s! The most popular ones include WineFest at St. Michaels in April, St. Michaels Brewfest in May, and the Wine & Food Festival and OysterFest in October.
  • Don’t forget to eat plenty of crab , oysters , and other local delicacies – it’s part of everyday life here on Maryland’s Eastern Shore, and it’s no different at the best St. Michael’s restaurants .

The Best Place to Stay on Maryland’s Eastern Shore

Though spending a day in the charming town of St. Michael’s is a wonderful thing to add to your itinerary to Maryland’s Eastern Shore, there’s something other-worldly about staying on our 70 zen-like acres near Rock Hall, MD. Our Eastern Shore Bed and Breakfast is rated as one of the best places to stay, and it won’t take you long to see why for yourself.

Maryland’s Eastern Shore is an easy escape from crowded cities like Baltimore, Washington D.C., and Philadelphia – and no matter the time you visit, you’ll find this beautiful part of the world serves as the tranquil and refreshing paradise you’ve been looking for.

Our Bed and Breakfast on Maryland’s Eastern Shore offers so much more than a comfortable place to call home at the end of the day. Though our accommodations are exceedingly comfortable, you’ll find that staying here goes far beyond a simple place to sleep. The amenities included in your stay, attention to detail, and exceptional hospitality work in concert to set our Eastern Shore Bed and Breakfast apart from its competitors.

Moreover, we’ll prepare you a fresh and delicious breakfast each morning of your stay. It’s the perfect fuel for whatever adventure lies ahead, including a day trip to the quaint town of St. Michael’s. Though you aren’t very far away from bustling metropolises, you’ll feel like you’re on an entirely different plane. It’s one of the best parts about staying with us on Maryland’s Eastern Shore. Isn’t it time you booked your room at our luxury Bed and Breakfast?

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day trips maryland eastern shore

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We are located on the serene and picturesque Eastern Neck of Maryland. Our location is just two hours away from Philadephia, Washington D.C., and Baltimore. Guests come for the quiet of nature and the gentle breezes of Chesapeake Bay.

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day trips maryland eastern shore

RESERVATIONS

Sunshine Whispers

50 Perfect Maryland Day Trip Ideas!

day trips maryland eastern shore

These 50 Perfect Maryland Day Trip ideas are really a great way to explore The Old Line State. There are so many ways to have fun in Maryland. These are all excellent ideas!

The State of Maryland really is America in Miniature. Maryland is a rather small state but wow, it’s jam-packed with fun things to do! One day you can visit a world class museum and the next you could be hiking the Appalachian Trail. There are mountain regions, more beaches than you could ever hope to visit, and a state that is full of historical significance. 

So, where should you even start? Well, I have picked out 50 perfect Maryland day trip ideas for you. These are all places we have visited and loved. And I think you will love these places too! Happy exploring!

Note: There is a Google Map with all these locations at the end of the post!

Kid Friendly Maryland day trip planning app

1. Swallow Falls State Park

This is one of the best, if not the best state park in Maryland. If you take the very kid friendly Canyon Trail you can hit not one, but 4 gorgeous waterfalls in one hike!  | Website

Related: Kid Friendly Guide to Swallow Falls State Park

swallow falls state park guide

Related: The Best Maryland State Parks for Families!

2. Deep Creek Lake State Park

Spend the day playing in the water and sand at this beautiful mountain lake. You can rent kayaks, there are playgrounds, numerous kid friendly trails, and the newly renovated Discovery Center at the park. | Website

Related: Best Deep Creek Lake Area Hikes for Kids

deep creek lake state park

3. Track’s and Yaks

One of the coolest and most unique outdoor adventures that literally the entire family can enjoy. Have you ever been rail biking? It’s the perfect way to experience a gorgeous area of Maryland. | Website

Related: Kid Friendly Guide to Track’s And Yaks!

rail biking traks and yaks

4. C&O Canal Williamsport/Cushwa

Bring your bikes and scooters! You can easily get on the C&O Canal trail from the Williamsport location. Also, when it’s open, the Cushwa visitor center has great activities for kids! | Website

williamsport

Related: Best Maryland Lakes for Swimming

5. Hagerstown City Park

This park has so much to offer families. There are two large playgrounds, with one of them being very updated with fun features your kids will love to slide, zip, and climb on. You can feed the ducks (there are loads of ducks), and pop into the FREE Fine Arts Museum! | Website

hagerstown city park

Related: Kid Friendly Guide to Jellystone Park in Williamsport, MD

6. Weverton Cliffs

If you are up for a challenge you will definitely be rewarded. This 1.5 mile each way hike brings you to one of the best overlooks in Maryland! | Website

day trips maryland eastern shore

7. Greenbrier State Park

Our best pick for lake swimming in Maryland. The beach is fairly large with a shallow sandy bottom. This is perfect for toddlers and younger kids. There are also some nice kid friendly hiking trails around the lake! | Review of Greenbrier

greenbrier state park beach

8. Gathland and Gambrill State Parks

Two Maryland State Parks that are super close to each other. Gambrill State Park has great overlooks and super kid friendly hikes. Gathland State Park is home to the very instagrammable War Correspondents Arch. There are some great Civil War displays and this park plugs into the Appalachian Trail! | Gathland Website | Gambrill Website

gathland state park

9. Antietam National Battlefield

The site of the bloodiest day in US History. Take the driving tour to get a sense of the battle, and get out and stretch your legs.  | Website

day trips maryland eastern shore

Related: Best Playgrounds and Parks in Frederick County, MD

10. Cunningham Falls State Park

This park is great for families because there is a super easy hike to Cunningham Falls. Then, after the hike you can cool off at the beach/lake swimming! | Website

cunningham falls

Related: 8 Gorgeous Maryland Waterfalls

11. Walkersville Southern Railroad

Check the Walkersville Southern Railroad website for special events that range from Bunny trains, Santa trains, Superheroes, Princesses, Teddy Bears and more! This train is very kid friendly and the countryside is just so lovely! | Walkersville Review

day trips maryland eastern shore

12. Tree Trekkers

Do you have a climber? If so, you definitely want to make a reservation to check out this aerial adventure park. There are various levels for younger kids all the way up to teens and adults! | Website

day trips maryland eastern shore

13. Baker Park and Carroll Creek Linear Park

There are so many fun shops and restaurants in Downtown Frederick. If you visit, don’t miss the chance to walk along the canal at Carroll Linear Park and then play at Baker Park! | Website

day trips maryland eastern shore

14. Glen Echo Park

Glen Echo Park was once an amusement park and is now preserved as part of history. You can still ride the carousel (in season), visit the aquarium, play on the playground, and attend a kid friendly show at either Puppet Co. or the Adventure Theatre MTC. | Website

day trips maryland eastern shore

15. Great Falls

The Maryland side of this national park has numerous outstanding waterfall overlooks, access to the C&O Canal towpath, and some super fun hikes. Test your rock scrambling skills on the Billy Goat Trail! | Website

great falls

16. Wheaton Regional Park

What’s not to love at this park in Silver Spring? Your kids can spend a few hours playing on the massive Adventure Playground. Pack a picnic lunch, and then ride the miniature train and historic carousel. If you still have energy, pop over to the adjacent Brookside Gardens for a truly lovely nature experience. | Wheaton Review

wheaton regional park

17. Adventure Park USA

Did you know there is a super fun amusement park in Frederick County? It has rides in the summer, tons of outdoor adventures, and even more fun indoors with ropes courses, bumper boats, laser tag, and more! | Website

day trips maryland eastern shore

18. Seneca Creek State Park

This is a great park for families because Lake Needwood is just totally gorgeous. Hike around the lake or rent a kayak or canoe and get out on the water. Then, let your kids burn energy at the super fun recycled tire playground! | Website

seneca creek

19. Watkins Regional Park

We’re off to see the wizard! Yep, Watkins Regional Park is home to the famous Wizard of Oz playground! But it’s also home to a second super fun horse racing playground, a fantastic nature center, miniature train, carousel, mini golf, and farm animals too! | Watkins Regional Park Review

Related: Ultimate Guide to the Wizard of Oz Playground

wizard of oz playground kansas

20. Jug Bay Nature Area

You will totally dig walking over the marshland on boardwalks and then meandering down the former railbeds. Along the way you can spot loads of wildlife including birds of all kinds, turtles, and more! | Website

jug bay trail

Related: 40+ Easy Hikes for Kids In Maryland!

21. Patuxent Research Refuge

Another fantastic nature preserve, Patuxent Research Refuge has an excellent visitor/nature center, and a gorgeous (and super kid friendly) hike around the lake. | Website

day trips maryland eastern shore

22. Piscataway Park

A great historic park to see amazing views of the Potomac. Take a hike on one of the kid friendly trails, and then pay a visit to the National Colonial Farm and say hi to all the animals! Check their website for when history reenactors will be on hand for demonstrations of life in the 17th and 18th century. | Website

day trips maryland eastern shore

23. Jefferson Patterson Park

This fantastic park in Calvert County has fantastic walking trails, a nature playground, visitor center, water access, and historical reenactment sites. A great place to spend a few hours or all day! | Website

jefferson patterson

Related: Kid Friendly Guide to Calvert Marine Museum

24. Blandair Regional Park

This super fun regional park in Howard County boasts not one, but three amazing playgrounds. The North Playground is likely the largest (and most impressive) playground in Maryland. And there is a Ninja Course that will challenge kids and adults of all ages! | Website

Related: Ultimate Guide to Blandair Regional Park

Spaceship themed play area Blandair north playground

Related: The Best Playgrounds in Maryland (sorted by County!)

25. Centennial Park

Bring your scooter! Walk/scoot around Centennial Lake and along the way play at one or more of their four impressive playgrounds! | Website

day trips maryland eastern shore

26. Baugher’s Orchard

Baugher’s Orchard is a pick your own heaven. Check the latest PYO crops and ride the tractor out to the picking fields. Afterwards, your kids will love exploring the petting farm and playground. And of course, make sure to pick up a treat from their bakery and snack shack! | Baugher’s Review

day trips maryland eastern shore

Related: Best Apple Orchards in Maryland!

27. Old Ellicott City

A great shopping and dining destination that has been devastated by flooding over the years. Still, you can visit a B&O Railroad Museum, grab some ice cream, hit up the fun kid friendly stores, and take a stroll on the Trolley #9 Trail. | Website

day trips maryland eastern shore

28. Patapsco Valley State Park

This sprawling state park has numerous areas to explore. Our favorite is the Avalon/Orange Grove area. Park near the swinging bridge to take a stroll (or bike ride) along the river on the Grist Mill Trail. Or, head up to Cascade Falls, which is a surprisingly short hike (you can make it longer by hiking beyond the waterfall). | Patapsco Avalon Area Guide

patapsco valley state park orange grove area

29. Kilgore Falls

This waterfall is so lovely it was featured in Tuck Everlasting. Bring your water shoes because one you hike the short distance to the falls, you will want to walk across the river to the other side, where you can get super close to the bottom and top of the falls! | Website

kilgore falls creek stomping

30. Ladew Topiary Gardens

You kind of have to see these gardens to believe them. The topiaries are really so cool.. Crazy what the gardeners do to form the bushes into creatures! The best part though (in my opinion) are the flowers and gardens themselves. There are so many fanciful gardens… you feel like the characters in A Secret Garden. In the springtime you can delight in azaleas, tulips, and more! | Website

Related: Kid Friendly Guide to Ladew Topiary Gardens

ladew topiary gardens

31. Havre de Grace Promenade

Park at either end of the promenade and walk along the water. Check out the Concord Pt. Lighthouse and your kids will definitely want to burn energy at the Millard-Tydings Park playground. It’s a super fun playground with loads of great play features! | Website

Related: Perfect Havre de Grace Day Trip

havre de grace day trip

32. Jerusalem Mill Village

Officially the headquarters of Gunpowder Falls State Park, Jerusalem Mill routinely has tours and activities on their grounds. It’s a living history museum. Bring your hiking shoes and swimsuits though. You can plug into trails for Lower Gunpowder Falls from here. And in the summer, the river is a very kid friendly place to go splashing and swimming! | Website

jerusalem mill village

33. Sandy Point State Park

Speaking of swimming, there is hardly anything more Maryland iconic than a beach day at Sandy Point State Park. Splash and play on the beach under the watchful eye of the Bay Bridge. | Website

sandy point state park

Related: Best Chesapeake Bay Beaches to Cool off this Summer!

34. Kinder Farm Park

In 2020, Kinder Farm Park renovated their playground to turn it from good to simple awesome. When you kids tire from playing, walk over to visit all the farm animals or hit the trails for a family friendly hike. | Website

Related: Kid Friendly Guide to Kinder Farm Park

kinder farm park anne arundel county

35. Port Discovery Children’s Museum

If you haven’t taken your kids to Port Discovery yet, you must take them asap! Port Discovery is one of the best children’s museums in the nation and for good reason. Our favorite exhibits include the SkyClimber, the Port, Tiny’s Diner, Adventure Expedition, and Wonder of Water! | Port Discovery Guide!

port discovery

36. Maryland Zoo in Baltimore

I have a love affair with the Maryland Zoo in Baltimore. This zoo is so accessible and fun for kids, especially younger kids. You can get really close to the animals and even feed the giraffes. There are numerous play features, and a lovely petting farm. | Maryland Zoo Guide!

penguins at maryland zoo

37. Maryland Science Center

Anchoring the Inner Harbor, the Maryland Science Center is basically a bonus Children’s Museum.. But one that appeals to kids from age 0-99. Every time we visit all the kids have a blast, regardless of age. There are exhibits that cater to all ages. And you have to check out both the Planetarium and the IMAX! | Maryland Science Center Review

A great Maryland day trip idea would be to combine the Maryland Science Center with a visit to the American Visionary Art Museum and Rash Field.

Related: 50+ Things to Do With Kids in Baltimore

maryland science center

38. Double Rock Park

This unassuming local park in Middle River is the best hidden treasure we have found. Go down to the river and climb all over the rocks and boulders. You and your kids will have a blast exploring! | Website

Related: Kid Friendly Guide to Double Rock Park

double rock park kid friendly trail guide

39. Oregon Ridge Nature Center

A super fun nature center with an excellent nature playground, historical exhibits, and kid friendly trails. Don’t miss the painted trees forest! | Website

oregon ridge nature center

Related: Fantastic Nature Centers in Maryland

40. Gunpowder Falls State Park Hammerman Area

Like Patapsco Valley State Park, Gunpowder Falls State Park has loads of areas to explore. If you want to play on a beach though, the Hammerman Area is where you want to go! | Website

day trips maryland eastern shore

41. Ft. Howard Park

This historical park is really fun and interesting. It’s on the water so that’s fantastic. There is a nice walking/biking path and two playgrounds. The super fun draw though are the battle emplacement ruins you can still explore. Very cool.. If not a little spooky. | Website

A fantastic Maryland day trip idea would be to combine a visit here with North Point State Park and Cromwell Valley Park.

day trips maryland eastern shore

42. Calvert Cliffs State Park

When you think of shark teeth hunting in Maryland, Calvert Cliffs State Park is probably at the top of your must-visit places. The walk is a little long for younger kids (3 miles round trip), but very flat and easy, with tons of interesting places to explore along the way. The small beach is the piece de resistance though. Bring buckets, shovels, and strainers and try to see if you can find a megalodon tooth! | Website

calvert cliffs

43. Annmarie Sculpture Garden

The Annmarie Sculpture Garden and Arts Center is totally awesome! Yes, I am gushing… it is that great. I wish we lived closer to Lusby, MD so we could visit more often. And don’t let the fact that it is a ‘sculpture garden’ dissuade you. This lovely garden is full of fun, whimsical, and downright enchanting activities for kids. The delightful Fairy Lolly is fantastic for imaginative play. There are public art projects and some really fantastic annual special events. | Annmarie Sculpture Garden Review

annmarie sculpture garden

Related: Best Shark Teeth Hunting Beaches in Maryland

44. Historic St. Mary’s City

️Historic St Mary’s City is a living history museum.. think Williamsburg but on a smaller scale. St Mary’s City used to be the capital of Maryland and the museum offers hands on glimpses into the 17th century life of area residents. Throughout the city there were demonstrators and docents to explain what life would have been like and offer hands on activities. This is a really unique and totally fun place to visit! | Website

A great Maryland day trip would be to combine a trip here with some fun in the sun at Point Lookout State Park.

day trips maryland eastern shore

45. Point Lookout State Park

Located and the tippy tip of Southern Maryland, Point Lookout stood vigil during the Civil War. Now you can spend a lovely day playing in the sand and cooling off in the water. | Website

point lookout state park

46. Elk Neck State Park

Elk Neck State Park in North East, MD is a treasure. The most iconic part of the park is the Turkey Point Lighthouse. The Turkey Point Lighthouse trail is a 1.9 mile loop trail (or you could do out and back directly from the lighthouse). If you do the loop trail, you will find numerous waterfront picnic and small beach areas. It is really such a lovely place to spend the day! | Website

If you want a great idea for a Maryland day trip, combine this with a trip to Plumpton Park Zoo and have dinner at Havre de Grace!

Elk Neck State Park

47. Tuckahoe State Park

This great state park is so much fun for both day trips and weekend trips! There are multiple areas to explore. The VisitorCenter has a great aviary, supplies for the disc golf course, and trailheads for over 20 miles of fun trails! 

At Tuckahoe Lake you can rent kayaks and canoes, fish, and kids will absolutely love the recycled tire playground! In the Campfire Loop area there are nature trails and another great playground with a fantastic slide! To make the perfect Maryland day trip, check out Adkins Arboretum next door and make a pit stop at the Idlewild Park in Easton, MD. | Website

Related: Best Things to Do With Kids on the Eastern Shore

tuckahoe state park

48. Ocean City Day Trip

Most people spend a few days or a week at this Atlantic Ocean resort town. However, a day trip is totally doable too! Many people get up early, hit the beach and boardwalk, and then head home after dinner. There are so many fun things to do in Ocean City! | Ocean City fun ideas!

ocean city vacation tips

Related: 100 Days of Summer Fun in Maryland!

49. Betterton Beach

Betterton, MD is a fantastic place to spend a Maryland day trip– especially if you have kids! The beach is amazing and doesn’t have jellyfish! There is a great community park with a fun playground. And just a short drive away you can pick fruit and get a scoop of homemade ice cream at Lockbriar Farms!

Related: Best Kid Friendly Betterton Beach Maryland Day Trip Itinerary

betterton beach day trip

50. Harriett Tubman Visitor Center and Byway

This important museum and visitor center is an excellent tribute to a national hero and civil rights legend. Bring your kids and start a conversation about racism, slavery, and equality. The exhibits are really well done and educational for kids and adults.

The mural pictured below is actually not a part of the visitor center. It’s located on the side of the Harriet Tubman Museum & Educational Center and stop #5 on the Tubman Byway road trip! A great Maryland day trip idea would be to combine these spots with a trip to the Chesapeake Maritime Museum and Blackwater National Wildlife Refuge. | Website

harriet tubman

Perfect Maryland Day Trip Map!

Related: The 100 Best Things to Do With Kids in Maryland!

FAQ about Maryland Day Trips

That depends on what you would like to do and if you are with kids or adults only. On a family trip our top picks are the Maryland Zoo in Baltimore, Maryland Science Center and Rash Field, or the National Aquarium. With or without kids ideas include the USS Constellation, the American Visionary Art Museum, and Ft. McHenry. For an adults only trip, check out Fells Point or Hampden.

The Deep Creek area in Garrett County, MD is between 3-4 hours from Baltimore, MD.

That depends on the traffic on the Bay Bridge. With no traffic you can reach Ocean City in 2-3 hours. However, with summer, weekend, or holiday traffic– plan to add at least 1 hour to your trip.

Our top picks for day trips within 3 hours of Baltimore include Washington D.C., Philadelphia, PA, Lancaster County, PA, the Eastern Shore and Chesapeake Bay (not necessarily just Ocean City!), and Frederick County, MD.

The Maryland Department of Tourism splits the state into 5 regions: Capital, Central, Western, Southern, and Eastern.

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maryland day trip ideas

Hi! If you love to have fun with your kids and explore, create, travel, laugh, and love.. you have come to the right place! Follow along to get great tips for fun in Maryland, family travel destinations, and other family fun ideas!

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day trips maryland eastern shore

We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md.

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We Sail April 19,2024 to Nov 3, 2024

Clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

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St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

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Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

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Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

day trips maryland eastern shore

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips Lyon Rum

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips raising the sail

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips guests taking a turn at the wheel

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions romantic date night

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions people having fun

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina, a true symbol of excellence and commitment to providing the best sailing and boating services - Our passion for sailing has led us to achieve the highest standards and earn a Gold Medal award, representing our unwavering dedication to exceeding our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unparalleled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Savor the taste of luxury of hand picked wines available on all our St Michaels boat rides. Sail Selina offers both reds and whites, providing the ultimate sailing and wine tasting experience on the Chesapeake Bay - This stunning image showcases the elegant and refined design of Sail Selina's etched wine glasses, a perfect complement to our premium wine tastings and luxurious sailing adventures - With a variety of wine tasting packages to choose from, Sail Selina offers a unique and personalized experience for wine enthusiasts and sailing aficionados alike - Fall in love with the rich flavors and aromas of the finest local and international wines, as you sail in style aboard our comfortable and well-equipped boats - Book now and discover the unrivaled taste of luxury and elegance with Sail Selina, the premier wine tasting and sailing adventure on the Chesapeake Bay

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina. Our quality has achieved the highest standards and has been rewarded with a quality ribbon, representing our commitment to excellence and dedication to providing the best sailing and boating services – It is a symbol of our passion for sailing and our mission to exceed our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unrivaled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

day trips maryland eastern shore

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Experience the thrill of the journey with Sail Selina's ship's wheel, the ultimate symbol of adventure and maritime history - This stunning image captures the timeless elegance and authenticity of Sail Selina's ship's wheel, a testament to the classic and refined design of the sailing vessel - With our skilled and experienced crew at the helm, enjoy the excitement and thrill of sailing on the Chesapeake Bay, as you witness the power and precision of the ship's wheel in motion - Fall in love with the rich and storied history of the high seas, and experience the magic of sailing aboard an iconic and timeless wooden sailboat - Book now and discover the wonder of the ship's wheel of Sail Selina, an experience that will transport you to another time and place!

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

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USA TODAY 10Best

A perfect weekend in Easton, Maryland: Where to eat, drink, and stay

Sarah Maiellano

April 25, 2024 // By Sarah Maiellano

By Sarah Maiellano April 25, 2024

Easton, Maryland, is full of charm and history

Maryland's Eastern Shore along the Chesapeake Bay is a playground for sailors, seafood lovers, and sunset chasers. Easton, Maryland, a charming, walkable town that punches well above its weight regarding cultural attractions and dining, is a must-stop. A short drive from Washington, D.C., Baltimore, and Philadelphia, Easton might not be on the water, like nearby St. Michael's, but the coastal feel is there.

The town comes alive in the summertime when vacationers descend to enjoy the area's waterways, villages, and local crab and oysters. But its history, charm, and colonial and Victorian architecture make this a year-round destination. No wonder it's been a top contender for Best Small Town Cultural Scene and Best New Year's Eve Drop in the USA TODAY 10Best Readers' Choice Awards.

Here's where to go, what to do, and where to stay in Easton, Maryland.

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Things to do in Easton

The collection spans centuries at Easton, Maryland's Academy Art Museum

For a small town, Easton is rich in arts and culture. At the restored 100-seat Ebenezer Theater , celebrated musicians from around the world take the stage. The 400-seat Avalon Theatre hosts touring bands in an art deco venue a few blocks away.

Founded by a group of local artists in the 1950s, the Academy Art Museum features a wide-ranging collection, from Marc Chagall and Mary Cassatt to contemporary artists. The mix of 19th century and new architecture includes a beautiful two-story glass atrium. Catch special exhibitions that showcase works from modern masters and emerging artists alike.

Frederick Douglass is a beloved son of Easton, Maryland

Easton was involved in some meaningful moments in Black history, particularly those involving Frederick Douglass and Harriett Tubman, who were both born in this area.

Take self-guided driving tours of important moments in Douglass' life, including the abolitionist's early days on the Eastern Shore before he escaped enslavement and returned as a local hero.

Don't miss the Harriet Tubman Underground Railroad Visitor Center , about 30 minutes south of Easton. This national park site tells the story of Tubman's life, from the time of her enslavement in Maryland to her brave Underground Railroad missions and beyond.

Where to eat in Easton, Maryland

Bas Rouge in Easton, Maryland is led by a James Beard Award finalist

The ultimate destination on the Eastern Shore is Bas Rouge . Led by James Beard Award finalist Harley Peet and former staff from New York City's Le Bernardin, Bas Rouge exudes elegance. Rare ingredients dot the prix fixe menu in this glowy, high-ceilinged space, while sommelier-led wine pairings complement each course. You must order post-dinner cheese and dessert, plated tableside from rolling trolleys.

Bonheur features ice cream and crepes in a beautiful space

Bas Rouge's sister eateries should also be on your list. Bonheur serves ice cream, pie, high tea, and morning crepes in a whimsical, picture-perfect space. Sunflowers & Greens specializes in fresh, create-your-own salads, some with high-end ingredients like savory prosciutto.

Locals enjoy tiki-themed Tiger Lily for brunch. For lunch, dining on the patio at Legal Assets , located in an 1867 carriage house, is a treat.

Where to sample wine and scotch in Easton

The Stewart has the deepest whiskey and Scotch collection in Easton, Maryland

On the same block as Bas Rouge, The Stewart takes its cues from Edinburgh. Its $1.5 million Scotch collection is set behind a curved bar in a cozy space with a central fireplace. Your best bet is to try one-ounce pours of a few different single malts — the knowledgeable bar staff will guide you. The menu is tight, with indulgent treats like fries topped with caviar and a grilled cheese stuffed with braised short rib.

The Wardroom is a busy wine, liquor, and cheese shop and a sit-down restaurant. During the day, come for cheese (aged in a 40-degree underground cave on-site) and charcuterie-filled lunches, and at night, it's all about fresh pasta. A self-serve wine tap system lets you sample well-sourced new and old-world wine.

Where to shop in Easton

Eclectic art hangs at Flying Cloud Fine Art Posters in Easton

All over town, large-format vintage posters decorate the walls of local businesses. Call it the Flying Cloud Fine Art Posters effect. This gallery and shop collects and sells colorful posters that hawk long-gone airlines and liquor brands. Next door, find bestsellers and a sweet children's section at Flying Cloud Booksellers .

Stroll around to find art galleries and lovely shops of all stripes, like Caroline Dalton's boutique, Arrae , known for fine jewelry, home decor, beauty products, children's items. Get in the coastal spirit at Sailor , which outfits shoppers in Lilly Pulitzer, Southern Tide, Patagonia, Vineyard Vines, and other brands perfect for seaside locales. Shopping for kids is easy at Crackerjacks , where owner Linda Laramy has sold unique toys to generations since 1979.

Benjamin offers all the shiny things in Easton

Benjamin is a must-stop whether you're a window shopper or have the budget to collect fine crystal, china, and silver. The gallery-style boutique literally sparkles.

A quick drive from downtown, pick up some Amish-style soft pretzels, pies, and fudge at Easton Amish Market . More than 20 vendors from central Pennsylvania sell their wares — including solid wood furniture — at this market.

Where to stay in Easton, Maryland

Tidewater Inn is centrally located in downtown Easton

You can walk to all of Easton's attractions from the Tidewater Inn. This centrally located hotel offers comfortable rooms in its main building and a historic mansion about a block away. Rooms take on distinct themes, like the Palmetto Suite and the French Suite.

The Hummingbird Inn , a bed and breakfast in an 1800s house, is also centrally located. Rooms here are spacious and guests enjoy gathering in a Victorian Garden with a fountain and a firepit.

For a next-level stay, drive 10 miles to the Inn at Perry Cabin in the buzzy neighboring town of St. Michael's. You might recognize it as the waterfront filming location of the film, "Wedding Crashers." Named the most romantic inn in the U.S. by 10Best readers, this luxury property features a spa, golf, tennis, sailing, and a popular seafood restaurant.

Sarah Maiellano

About Sarah Maiellano

Sarah Maiellano is a Philadelphia-based freelance writer covering travel, food, wine, and more. She was born and raised in Philly and lived in Washington, D.C. for 10 years.

Read more about Sarah Maiellano here.

Connect with Sarah via: Website | Instagram

The 5 best day trips from Baltimore

Julekha Dash

Aug 25, 2021 • 6 min read

day trips maryland eastern shore

Escape the bustle of city life with these quick day trips from Baltimore © Greg Pease / Getty Images

One of the biggest advantages of living in Baltimore is the ease of escape to the region’s smaller towns and rural enclaves. Just a short car ride away and Baltimoreans can explore the historical and natural wonders of western Maryland, Pennsylvania, Virginia and the Eastern Shore. Whether you opt to stay the day or even the weekend, here are the best day trips from Charm City. 

St. Michael’s, Maryland 

Why go: Explore maritime history

St. Michael’s, known as “The jewel of Maryland’s Eastern Shore ”, captivates visitors with its tranquil, sailboat-lined waterfront and historic buildings that come in a variety of architectural styles. 

Wander through the town’s two museums, the St. Michael’s Museum which offers walking tours that highlight abolitionist Frederick Douglass’ formative years in the town, while the Chesapeake Bay Maritime Museum includes a lighthouse and working shipyard in a picturesque waterfront park. 

View across the harbor at St. Michael's Chesapeake Maritime Museum.

Visitors can learn about the town’s history on the water, by taking a Patriot Cruises’ narrated ride along the Miles River. 

After sightseeing, eat and drink your way through the town. Start with a visit to Eastern Shore Brewing to sample the flagship St. Michael’s Ale, or Saint Michael’s Winery, where you can taste the red, white and rosé wines outside. 

St. Michael’s is full of charming restaurants that feature Chesapeake Bay seafood, including Bistro St. Michaels and Ruse, which serves a seasonal menu filled with oysters and rockfish. You’ll find Ruse inside the area’s newest inn, the Wildset Hotel , an airy, historic property spread across three buildings on the town’s main street.

How to get to St. Michael’s: The one-and-half-hour trip takes you through I-97 to US 50 all the way to Eastern Shore town. 

The best time to visit Baltimore

View of Carroll Creek and downtown Frederick Maryland from Baker Park

Frederick, Maryland

Why go: Enjoy some quiet time in the outdoors   

There’s some debate as to whether Frederick is still considered part of Western Maryland as it now houses so many Washington, DC commuters. But in any case, the town offers a perfect getaway for vacationers looking for a destination that is part country and part city.

Nature lovers will enjoy a stroll along Carroll Creek Park , which spans more than a mile through downtown with bridges and fountains along the way. It’s also a short 20-minute ride to Brunswick, where you can bike or walk along the historic Chesapeake & Ohio Canal. 

Urbanites will enjoy the town’s ample supply of vintage shopping and locally owned boutiques, breweries and dining destinations. Plan your trip around one of Chartreuse and Co. ’s open weekends to check out artisan-made goods, locally made wine and spirits, and a farmers’ market. While the dining options are endless, a good place to start is Thatcher & Rye , chef Bryan Voltaggio’s casual eatery that replaced his fine-dining venue Volt. 

Spanish tapas fans can head to Isabella’s Taverna & Tapas Bar while Mayta’s Peruvian Cuisine makes exceptional lomo saltado (strips of steak, onions, tomatoes and fries).

How to get to Frederick: It’s a straight shot on I-70 and takes less than an hour’s drive. Take a Greyhound bus to tour the walkable downtown car-free. 

The 10 best things you can do for free in Baltimore  

Exterior of the white brick historic Carlyle House in Alexandria, Virginia.

Alexandria, Virginia

Why go: Dive into American history 

Filled with colonial homes adorned with gas lanterns, museums and significant cultural sites, Alexandria draws history and architecture buffs. 

George Washington’s Mount Vernon , the first president’s estate, might be the best known, but the town houses several other landmarks, including the Greek Palladian-style Carlyle House mansion and the Stabler-Leadbeater Apothecary Museum , a former pharmacy whose bottles and herbal remedies remain preserved. 

Several guided walking tours offer visitors a chance to dive deep into the area’s history. Named for the papers that gave enslaved individuals their freedom, Manumission Tour Company has three tours that honor the legacy of Alexandria’s Black Americans who fought for freedom. 

Alexandria’s lively waterfront area has expanded with new waterfront tours and restaurants. Sail the Tall Ship Providence after dining on thoughtfully prepared tapas served in a waterfront pier with two shipping containers at Barca Pier & Wine Bar . 

To satisfy your sweet tooth, order a custard sundae from Gooodie’s Frozen Custard & Treats , located in a retro ice house. Spend the night at one of the boutique hotels, such as the Kimpton Lorien Hotel & Spa , or a historic property like the George of Old Town , decked out in colonial flair. 

How to get to Alexandria: Getting to Alexandria takes a little over an hour and the most direct route is to take I-295 most of the way there. Just avoid rush hour. It’s also an easy train ride on the Acela Northeast Regional, which will take an hour if you pick the shortest train ride.  

Blowers and harvest machines comb the vineyards drying and plucking grapes for winemaking after a downpour at Barboursville Vineyards in Gordonsville, Virgina

Gordonsville, Virginia

Why go: For the wineries 

The centrally located town of Gordonsville in Orange County, Virginia makes a good base to start your weekend journey in Virginia’s Blue Ridge Mountains , known for its unparalleled vistas, quaint Main Streets and scenic wineries. 

Wander the brick-lined, flower-pot-strewn historic district in Gordonsville filled with antique shops, clothing stores and art galleries. 

The town’s newest restaurant, Champion Ice House , serves fried chicken while Well Hung Vineyard offers a tasting room and restaurant in downtown Gordonsville. Unwind at the neighboring Barboursville Vineyards , which serves a rotating list of reds, whites and rosés in an 18th-century country estate with a restaurant and cottages where you can spend the night.

Don’t leave without visiting the Market at Grelen in Somerset, a garden shop, café and pick-your-own farm with picturesque hiking trails. 

How to get to Gordonsville: There are a few different ways to get there. The shortest route involves taking I-95 South to I-495 West to I-66 South to US 29 South. 

A pair of horses pull a plough on a large farm in Lancaster, Pennsylvania

Lancaster, Pennsylvania

Why go: For the Amish culture 

Horse-drawn buggies and white barns dot the Amish countryside surrounding Lancaster . There are  Several companies   that will take visitors on guided tours to see the rural landscape up close and stop at local country stores where you can pick up homemade whoopie pies and other baked goods. 

Tour an 1840s Amish farm with a school, blacksmith shop and smokehouse at the Amish Village . 

Operating since 1730, the Lancaster Central Market offers a smorgasbord of culinary offerings, from produce to meat, poultry, sandwiches and ice cream. The area contains several notable restaurants, including Luca , serving Italian wood-fired dishes, and immersive dining experience Amorette.

How to get to Lancaster: Take I-83 to US 30 East, which will take a little over 90 minutes by car. An Amtrak train will take at least three hours with a stop in Philadelphia.  

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Top neighborhoods to explore in Baltimore  The best things to do in Howard County, Maryland   Spending diary: What I spent on a three-day road trip to Baltimore  

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Here Are 15 Unique Day Trips In Maryland That Are An Absolute Must-Do

day trips maryland eastern shore

Jamie Alvarenga

Jamie Alvarenga is a writer and editor who loves all things Maryland.

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Looking for a day trip in the Old Line State other than the city or beach? Here is a list of 15 unique day trips in Maryland that are an absolute must-do. While there are hundreds more options to choose from when it comes to unique destinations in Maryland, these 15 are a great place to start. Check each one off your Old Line State bucket list!

day trips maryland eastern shore

day trips maryland eastern shore

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day trips maryland eastern shore

What do you think of our list of the best day trips in Maryland? How many of these places have you been to? For more fun destinations, check out these 12 awesome vacations to take in Maryland .

If you think we’ve missed an amazing must-see attraction in Maryland, nominate it here , and we’ll be sure to check it out!

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

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Day trips near me in maryland.

Where can nature-lovers go for the best day trips in Maryland?

These are the best day trips for nature lovers in Maryland:

  • Assateague Island
  • Swallow Falls State Park
  • Sandy Spring Adventure Park

If you love hiking, it's hard to top the stretch of the Appalachian Trail that runs through Maryland! Almost 40 miles of this National Scenic Trail cross through the Old Line State. Other amazing places for hiking in Maryland include Calvert Cliffs State Park and Patapsco Valley State Park. If you're looking for a way to enjoy nature with young children, the Baltimore Aquarium is one spot you've got to visit.

What are the best scenic drives in Maryland?

The best scenic drives in Maryland are:

  • Hoopers Island Road
  • Interstate 68 through Sideling Hill
  • Interstate 70 through Western Maryland

Maryland's back roads showcase all sorts of natural beauty, whether you drive them in the spring and welcome the wildflowers back, or in the fall when the colors of the season begin to burst onto the mountainsides. Here are a few of our favorite scenic drives in Maryland that you've got to check off your bucket list.

What are the top must-visit attractions in Maryland?

The best attractions in Maryland are:

  • National Aquarium
  • Fort McHenry
  • Baltimore Museum of Art
  • Antietam Battlefield

There are a handful of must-visit attractions in Baltimore, like the National Aquarium, Fort McHenry, and the Baltimore Museum of Art - oh, and the Old Bay Store, because let's be real, that's more important to us than art. Swallow Falls State Park is a spot that deserves a place on your bucket list thanks to its beautiful waterfall - but don't worry, it's hardly ever packed with crowds. If you're looking for coastal attractions, visit Smith Island for a slice of famous cake, or head to Ocean City, Maryland to enjoy restaurants, entertainment, a boardwalk, and beaches. Finally, be sure to visit Antietam Battlefield for a glimpse at history and perhaps an encounter with the paranormal.

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Where Harriet Tubman's Story Begins

Take a powerful and inspiring road trip to the places on maryland’s eastern shore and through delaware where harriet tubman lived, worked, worshiped, and led others out of slavery. in 2022 the world celebrates the bicentennial of tubman's birth., take a powerful and inspiring road trip to the places on maryland’s eastern shore and through delaware where harriet tubman lived, worked, worshiped, and led others out of slavery..

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Welcome to the Tubman Byway

Maps & guides, to explore the byway.

Experience Tubman’s story through the road trip known as the Tubman Byway. This self-guided, scenic driving tour includes more than 30 sites, many of them with outdoor markers or interpretive signs that share the story of that place, and winds for 125 miles through Dorchester on Maryland’s Eastern Shore before into Delaware and ending in Philadelphia, where Tubman first found freedom.

Highlights include the Harriet Tubman Underground Railroad State Park and Visitor Center , The Harriet Tubman Museum & Educational Center (home of the Harriet Tubman Mural), the Dorchester County Courthouse (with its magnificent, new bronze sculpture honoring Tubman). Learn more about the sites through our free Map & Guide and free audio guide .

The byway in Dorchester County also includes Brodess Farm , where Harriet spent her early years; Bucktown General Store , where Harriet’s life changed forever.  

History Savers

day trips maryland eastern shore

Renna is a history saver, and just one of many fascinating people you might meet along the Byway.  Read her story on VisitDorchester.org .

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Harriet Tubman - Freedom Graphic

Updated March 1, 2024 Harriet Tubman's funeral in 1913 in Auburn, New York. Celebrate Harriet Tubman in the land where she was born this March. Harriet [...]

U.S. Postal Service Underground Railroad stamps

UGRR stamps to be dedicated at Harriet Tubman Day March 9

Join in the Harriet Tubman Day celebration on March 9, 2024 at the Harriet Tubman Underground Railroad State Park & Visitor Center in Church Creek, MD. The highlight will be the official, national dedication of the new U.S. Postal Service stamps that feature Tubman and nine other Underground Railroad heroes!

African American Heritage Mural - by Michael Rosato - Cambridge, MD

Celebrate Black History Month in Harriet Tubman Country on Maryland’s Eastern Shore

The area along the Harriet Tubman Byway on Maryland's Eastern Shore is filled with Black history and culture – from Harriet Tubman to civil rights. That means there is lots to explore for Black History Month – and every other month of the year, too, especially in Dorchester County, Maryland – birthplace of Harriet Tubman....

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Maryland Fishing Report – April 24

Zach Bennett caught this northern snakehead in the Patapsco River. Photo courtesy of Zach Bennett

Zach Bennett caught this northern snakehead in the Patapsco River. Photo courtesy of Zach Bennett

The weather forecast for the next week promises mild and sunny conditions, perfect for venturing into the outdoors for fishing with family and friends. Trout continue to be stocked each week in the put-and-take trout waters, and a wide variety of fish are active, including the northern snakehead .

Forecast Summary: April 24 – April 30:

Stable, moderate weather this week will make for great fishing conditions to enjoy the variety of fish currently swimming in Maryland’s waters. Main Chesapeake Bay surface temperatures are holding in the high 50s. River temperatures have also risen to the upper 50s and low 60s, although smaller streams and downwind areas will warm faster on a sunny day and can hold temperatures even warmer. Such low salinity areas will be prime areas to look for hickory and American shad as they move upriver to spawn. Keep an eye out for large gamefish ambushing the shad as they move upriver. 

Expect above average flows for the Potomac and Susquehanna rivers but average flows for most of the other Maryland rivers and streams. Expect poor but improving water clarity for the Maryland portion of the Bay down to the Bay Bridge as well as the Potomac River down to the 301 Bridge. To see the latest water clarity conditions, check Eyes on the Bay Satellite Maps . There will be above average tidal currents through Tuesday as a result of the full moon on April 24.

For more detailed and up-to-date fishing conditions in your area, continue to check out Click Before You Cast .

Flows at the Conowingo Dam have moderated this week, but waters remained stained. Anglers are seeing the hickory shad runs peaking this week in the lower Susquehanna and Octoraro Creek. Anglers are also catching hickory shad at the mouth of Deer Creek. A few American shad are being caught close to the Conowingo Dam pool. Anglers are urged to bring a variety of colors in their shad dart inventory as well as small gold and silver spoons. Sun conditions and water clarity can have a large effect on color preferences that will attract the attention of hickory and American shad.

Decreased flows at the Conowingo Dam have attracted anglers looking to fish for flathead catfish in the turbine wash. Most are casting heavy jig heads with soft plastics and a strip of gizzard shad for the largest success. Flathead catfish can also be found just below the dam pool and as one moves down the river a transition occurs where blue catfish begin to dominate the catches. 

Blue catfish with a mix of large channel catfish can be found from the lower Susquehanna River south through the entire upper bay region to the Bay Bridge. Most of the blue catfish being caught are large and they tend to be spread out along channel edges. Many anglers are heading out in boats with family and friends and enjoying plenty of fun fishing during the striped bass closure. Shore anglers can access various public and private piers and docks along the shores of the upper bay region and its tidal rivers. Sandy Point State Park is a great place to fish for blue catfish for those with light to medium surf fishing tackle at the point locally known as the “rips” or from the jetty near the Bay Bridge. 

Cut bait is a popular bait of choice but chicken liver and chicken breast meat scented with various scents including WD-40 are working well. The Maryland DNR website provides a wealth of information on blue catfish , including how to fish for them and how to prepare them for the dinner table. 

Fishing for white perch is good this week in many of the tidal rivers and creeks of the upper bay, usually several miles below the spawning reaches. Fishing with small spinnerbaits and Roadrunner type lures is a great option. Bottom rigs baited with grass shrimp or pieces of bloodworm are also popular for deeper waters.

Photo of several fish on the back of a truck

Tailgating with some white perch, photo by Keith Lockwood

Anglers in the middle Bay are finding blue catfish along the channels in the bay this week due to the low salinity values due to spring runoff of freshwater. Locations near the Bay Bridge, Hacketts Point, the Brick House Bar area, down to Tilghman Island and the mouth of the Choptank River. Most of the blue catfish being caught are large, usually from 15 pounds up to 30 pounds or more. Cut bait of menhaden is a popular choice for bait but many anglers are having good success with chicken liver and chicken breast meat cut into chunks and soaked in various scents. 

The Choptank River has one of the largest blue catfish populations in the middle bay region and offers anglers good fishing in a more sheltered setting than fishing out on the open waters of the bay. One can fish from boats as small as a kayak or from the shores. The sections of the river from Denton to the town of Cambridge offer some of the best fishing along the channel edges this week.

Fishing for white perch in the tidal rivers of the middle bay region is good this week in several of the region’s tidal rivers. Anglers are having fun casting a variety of small spinnerbaits and jigs in the narrower sections of the rivers. Fishing with grass shrimp or pieces of bloodworm on a simple bottom rig is also an excellent way to fish for them in deeper waters. The Choptank River has recently been a good place to fish with grass shrimp on a bottom rig for white perch. One unfortunate consequence of fishing with small baits are 14-inch blue catfish that keep gobbling up the small baits.

Photo of fish on a hook

White perch, photo by Eric Packard.

Anglers in the Bay are focusing on catching blue catfish throughout the region and enjoying the catch-and-release fishery for hickory and American shad in the Potomac this week. Fishing for blue catfish has hit high gear as water temperatures warm and the catfish are becoming more active. The hickory shad spawning runs in the Potomac in the District of Columbia waters is peaking this week and American shad will linger a bit longer. Colorful shad darts and small gold and silver spoons are popular lures for those using spinning gear and fly-fishing tackle. 

The tidal Potomac River from the Wilson Bridge downriver to as far as the mouth of the river is providing plenty of blue catfish action. The Patuxent River from Jug Bay south to Benedict is an excellent place to fish, and the Nanticoke River near Sharptown is the place to be on the Eastern Shore. It should be noted that the Wicomico and Pocomoke rivers are also holding expanding populations of blue catfish.

Anglers can find good shoreline fishing locations at many of these areas, it will just take some exploring for newcomers. Others are out in their boats and even kayaks in the more protected waters and enjoying good fishing. Most anglers are using cut bait with circle hooks with or without a small inline float and a fish finder sliding sinker rig. Using a bait caster type spinning reel or putting a conventional reel on free spool and the clicker helps a circle hook do its job. Cut gizzard shad, menhaden, or white perch are popular baits as are chicken liver and scented chicken breast. 

Anglers are finding white perch in the tidal rivers several miles below the spawning reaches as they head towards the mouth of the tidal rivers and nearby bay waters. In shallower water casting a variety of small spinnerbaits and jigs is a great way to target them with light spinning tackle. In deeper waters a simple bottom rig baited with grass shrimp, or pieces of bloodworm can work wonders when targeting white perch moving down the rivers.

Put-and-take trout anglers continue to enjoy the continued generous stocking of trout in many of the trout management waters. Trout waters in the central, southern, and eastern regions with marginal summer water conditions will continue to be stocked through a good part of May, so anglers are urged to make time to get the family out to local community ponds that are being stocked. Several ponds and creeks in Montgomery and Baltimore counties were stocked recently. To see the latest stockings see the Maryland DNR trout stocking website . 

The Susquehanna and Potomac rivers have been experiencing high flows and plagued with stained waters for several weeks now. There is no forecast of rain for the next week so hopefully water flows and water quality will improve. Fisheries biologist Josh Henesy sent us a report from the upper Potomac late last week: “ Water levels are high, but color is fishable and ideal for smallmouth – which should be the most sought-after fish right now.  The bass seem to be moving into spawning areas but based on our collections, are still several weeks away from spawning. Water temps are in the upper 50s to 60 degrees, and with this level, color, and time of year, spinnerbaits would be my number one choice!”

Photo courtesy of Gina Maxwell

Angler Gina Maxwell caught a 34-inch Northern Snakehead in Galloway Creek on Apr 16,Photo courtesy of Gina Maxwell

Fishing for largemouth bass is very good this week in both tidal and nontidal waters. Largemouth bass are in a pre-spawn mode of activity. In the southern, central, and eastern regions, male largemouth bass are preparing spawning beds and females are holding in slightly deeper waters and feeding aggressively. Casting spinnerbaits and plastic worms are two excellent lures to use. Emerging grass beds and sunken wood are two excellent places to target. 

Northern snakeheads are becoming active and especially the larger ones. They can be found near any kind of structure or emerging grass beds, fallen branches and brush submerged in the water along shorelines are excellent places to target. Casting white paddletails, chatterbaits with large creature soft plastics as trailers and frogs are very popular lures. Dead sticking a large minnow under a bobber is always a great tactic while casting lures, just be sure to keep an eye on that bobber. On sunny afternoons sun exposed waters are a good location to look for northern snakeheads looking for a little warmth. 

The middle to upper sections of the tributary rivers in the upper bay are providing some exciting northern snakehead opportunities. The middle and Bush rivers are particularly good. The tributaries to the Potomac, the lower Dorchester County backwaters and tidal waters throughout the Chesapeake all have a number of northern snakeheads present.

Chain pickerel are providing plenty of fun and exciting fishing and can be found in the upper sections of most all tidal rivers, and nontidal ponds and reservoirs. The thick grass beds of the summer months are forming but there is still plenty of open water to find chain pickerel lurking near sunken wood and similar structures. Spinners, spoons, paddletails and jerkbaits are all good lures to use but consider removing the treble hooks and replacing them with single inline hooks. Chain pickerel have a habit of engulfing baits and often get hooked in the gills which is usually fatal.

Black drum are starting to show up in the surf and surf casters are soaking baits of sand fleas and clams, hoping to tie into one. These are usually black drum in the 15-pound to 40-pound size range and generally make for good eating. A few striped bass are being caught in the surf, but it will be another week or two before the Chesapeake Bay spawners pass by on their trip to New England waters. In the meantime, clearnose skates and dogfish are keeping anglers busy.

Fishing for tautog along the Ocean City Inlet jetties and the Route 50 Bridge and bulkheads has been very good this week. Anglers are catching plenty of tautog measuring over the 16-inch minimum. The daily limit is four fish and catching 3 or 4 legal-sized tautog is not uncommon. Sand fleas and pieces of crab are the most popular baits.

Striped bass are entertaining anglers casting soft plastic jigs and paddletails in the inlet, the Route 50 and 90 bridges. Most come up a little shy of the 28-inch minimum but offer plenty of fun catch and release action and now and then a legal-sized striped bass is caught. There are even a few large bluefish to be found inside the Ocean City Inlet and despite cold water and churned up bay waters a few flounder have been caught in the Thorofare Channel. Tautog continue to be the main attraction at the offshore wreck and reef sites this week. Anglers are catching a mix of medium to large tautog on pieces of crab.

“The woods are made for the hunters of dreams, the brooks for the fishers of songs.” – Sam Foss

Maryland Fishing Report is written and compiled by Keith Lockwood, fisheries biologist with the Maryland Department of Natural Resources . 

Click Before You Cast is written by Tidewater Ecosystem Assessment Director Tom Parham.

This report is now available on your Amazon Echo device — just ask Alexa to “open Maryland Fishing Report.” 

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  4. A Visitor's Guide to the Eastern Shore of Maryland

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  5. 10 Reasons the Eastern Shore of Maryland is a GREAT Getaway

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COMMENTS

  1. Things to Do on the Eastern Shore

    2 Reach the Dreamy Beach. 3 Indulge at the Boardwalk. 4 Visit Chesapeake City Historic District. 5 Spend a Day at the Races at Ocean Downs. 6 Experience the Crab Capital. 7 Marvel at the Untamed Chesapeake at Blackwater National Wildlife Refuge. 8 Walk in the Footsteps of Harriet Tubman and Frederick Douglass.

  2. 12 Great Day Trips to Maryland's Eastern Shore

    1. Eat Crabs on the Water. Perched on docks overlooking the Miles River, the nearly 60-year-old, family-­owned Crab Claw (304 Burns St., St. Michaels) is an Eastern Shore institution, serving steamed crabs, crabcakes, oysters, rockfish, and more from the water, plus other items such as a Beyond Burger. Tip: After feasting, stretch your legs ...

  3. Daytripping Through Maryland's Eastern Shore: 5 Perfect Day Trips

    Explore Historic Tilghman Island. Just 11 miles west of St. Michaels, separated from the mainland but connected via a drawbridge, Tilghman Island makes another beautiful day trip on Maryland's Eastern Shore. This scenic fishing village is known for its natural beauty, abundant boating opportunities, and some of the best seafood on the Eastern ...

  4. The Top Things to Do on Maryland's Eastern Shore

    The Maryland Eastern Shore, a peninsula extending hundreds of miles between the Chesapeake Bay and the Atlantic Ocean, offers endless recreational opportunities and is a popular summer vacation destination.Visitors from around the region flock to the Eastern Shore to explore its historic towns, beaches, and beautiful natural areas. Visitors can enjoy an array of activities, such as boating ...

  5. 25 Can't-Miss Places To Visit Along the Chesapeake Bay

    9 Chesapeake Bay Maritime Museum. 10 Cambridge. 11 Hart-Miller Island. 12 Dock Bars of the Bay. 13 Tilghman Island. 14 Hooper's Island. 15 Baltimore's Inner Harbor. 16 Blackwater National Wildlife Refuge. 17 Mallows Bay National Marine Sanctuary.

  6. 13 Things to do in Eastern Shore, Maryland

    Salisbury Zoo. Photo Credit: Deposit Photos. The Salisbury Zoo is one of the fun things to do in Eastern Shore, Maryland, for kids and families of all ages! You will find more than 100 animals from all over the world. The zoo offers close-up encounters with many creatures, from exotic species to native wildlife.

  7. Visit Maryland's Coast- Worcester County MD

    Visit Worcester County MD. Home of Maryland's Beach... and Beyond! Discover Maryland's only seaside offering the beauty of Assateague Island National Seashore and its wild horses. Explore authentic main street communities and the thrill of Ocean City. Experience serene nature sites, museums and heritage areas rich with local history, and our ...

  8. The 7 Best Things to Do on Maryland's Eastern Shore

    Hit the Beach. Of course, the most obvious way to enjoy the Eastern Shore of Maryland is to hit one of the beautiful beaches like Ocean City. This popular resort town sees up to 8 million visitors each year because of the multitude of things to do and its 10 miles of oceanfront beach. Just grab your towel, chairs and sand toys, park in one of ...

  9. How to Spend A Few Days on the Eastern Shore

    Spend A Day By The Water. Ocean City is a perfect introduction to the Eastern Shore. You'll find a party pretty much every season—from Winterfest to Springfest, Sunfest and beyond. While in Ocean City make sure you fit in a stroll along the award-winning Boardwalk. You'll find amusements, arcades, and plenty of snacks—like Fisher's ...

  10. 59 Best and Fun Things To Do In The Eastern Shore, Maryland

    This makes it an ideal location for lovers of history to learn more about what makes Maryland so special. Read on for our list of the best and most fun things to do in Eastern Shore, Maryland. The 59 Most Popular Things To Do In The Eastern Shore, Maryland 59. Piney Island. 4.0 ★★★★☆ (1 review)

  11. The 11 Very Best Day Trips You Can Possibly Take In Maryland

    Advertisement. 9. National Hard Crab Derby. Crisfield, MD 21817, USA. Facebook / The National Hard Crab Derby. The crabbiest festival in Maryland is located in Maryland's crab capital, Crisfield. The hard crab races are unlike anything you've ever seen. 10.

  12. Amazing Summer Day Trips to the Eastern Shore and Annapolis

    Just east of the Bay Bridge, this county is the Eastern Shore's answer to Key West. Two of the best party bars on the shore, Jetty Restaurant & Dock Bar (201 Wells Cove Rd., Grasonville; 410-827-4959) and Red Eye's Dock Bar (428 Kent Narrow Way N., Grasonville; 410-827-3937) , have water views, palm trees, live music, and crabs—and keep ...

  13. Day Trip to St. Michael's on Maryland's Eastern Shore

    Here's a roundup of eight of our favorite things to do in St. Michael's on Maryland's Eastern Shore: Get established in the town by taking a self-guided walking tour of St. Michael's on Maryland's Eastern Shore. Take historic narrated cruises through St. Michael's Harbor, or charter a boat and enjoy a sailing excursion in The ...

  14. Day Trips

    These trips are all trips that require only one day, or you can combine several into a trip lasting several days. State parks and wildlife management areas; Historical Landmarks; Cultural Landmarks; Blackwater National Wildlife Refuge - A must-see on the Lower Eastern Shore for the nature enthusiast. One of the largest populations of Bald ...

  15. 50 Perfect Maryland Day Trip Ideas!

    42. Calvert Cliffs State Park. When you think of shark teeth hunting in Maryland, Calvert Cliffs State Park is probably at the top of your must-visit places. The walk is a little long for younger kids (3 miles round trip), but very flat and easy, with tons of interesting places to explore along the way.

  16. Sail Selina II

    If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II's relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

  17. Eastern Shore Road Trips: 27 One-Day Adventures on Delmarva

    The first Secrets of the Eastern Shore guidebook is now available—it's called Eastern Shore Road Trips: 27 One-Day Adventures on Delmarva. Much more than a travel guide, Eastern Shore Road Trips is full of tales from days gone by and insights into the character and culture of the storied Delmarva Peninsula. Whether you're a road tripper ...

  18. Easton, Maryland: The best things to do, eat, and see

    Take self-guided driving tours of important moments in Douglass' life, including the abolitionist's early days on the Eastern Shore before he escaped enslavement and returned as a local hero.. Don't miss the Harriet Tubman Underground Railroad Visitor Center, about 30 minutes south of Easton.This national park site tells the story of Tubman's life, from the time of her enslavement in Maryland ...

  19. Best day trips from Baltimore

    St. Michael's, Maryland. Why go: Explore maritime history. St. Michael's, known as "The jewel of Maryland's Eastern Shore ", captivates visitors with its tranquil, sailboat-lined waterfront and historic buildings that come in a variety of architectural styles. Wander through the town's two museums, the St. Michael's Museum which ...

  20. The 15 Best Day Trips In Maryland That Everyone Should Take

    2. Antietam Battlefield. Antietam National Cemetery, 302 E Main St, Sharpsburg, MD 21782, USA. Mitchell Bishop/Google. The site of the bloodiest one day battle in American history, Antietam Battlefield offers plenty to explore. Walk through Bloody Lane, across Burnside Bridge, and check out the dozens of memorials.

  21. Where Harriet Tubman's Journey Began

    Experience Tubman's story through the road trip known as the Tubman Byway. This self-guided, scenic driving tour includes more than 30 sites, many of them with outdoor markers or interpretive signs that share the story of that place, and winds for 125 miles through Dorchester on Maryland's Eastern Shore before into Delaware and ending in Philadelphia, where Tubman first found freedom.

  22. Maryland Fishing Report

    Shore anglers can access various public and private piers and docks along the shores of the upper bay region and its tidal rivers. Sandy Point State Park is a great place to fish for blue catfish for those with light to medium surf fishing tackle at the point locally known as the "rips" or from the jetty near the Bay Bridge.