Things to Do in Eastern Shore in 2026

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Most popular activities in Eastern Shore

Tours & day trips

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Chincoteague: Assateague Island Sunset Boat Cruise

Free cancellation available

History & culture

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Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Free cancellation available

Attractions

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1 Hour Private Escape Room Experience in Ocean City

Free cancellation available

Food, drink & nightlife

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Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Free cancellation available

What to do in Eastern Shore

Discover the most popular places to visit in Eastern Shore

Ocean City Boardwalk

Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.

Ocean City Beach

Swim in the waves of the Atlantic Ocean, relax on soft white sands or stroll by the arcades and shops on the exciting boardwalk at this family-friendly city beach.

Jolly Roger Amusement Park

Bring your family to Jolly Roger Amusement Park and have a fun-filled day at this theme park in Ocean City. Amble around this family-friendly area's seaside, or seek out the golf courses.

Roland E. Powell Convention Center

Learn about the events happening at Roland E. Powell Convention Center during your trip to Ocean City. Stroll along the beautiful beaches or discover the beautiful sunrises in this family-friendly area.

Inlet Park

Explore the lovely green spaces of Inlet Park and enjoy the golf courses in Ocean City. Stroll along the seaside or discover the area's beautiful sunrises.

Carousel Ice Skating Rink

Enjoy a trip to Carousel Ice Skating Rink and popular activities like golfing in Ocean City. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

Jolly Roger at the Pier

The old classics get a new spin at this waterfront fun park, which has an exciting collection of wild rides, high-octane roller coasters and traditional amusements.

Northside Park

Enjoy the beautiful sunrises and explore Northside Park, a lovely green space in Ocean City. Wander the beautiful beaches and seaside in this family-friendly area.

Frontier Town Water Park and Golf

Bring the kiddos to Frontier Town Water Park and Golf and have a fun-filled day at this theme park in Berlin. Stroll along the beautiful beaches in this family-friendly area, or seek out the golf courses.

Discover the most popular landmarks and neighborhoods in Eastern Shore

The morning after a frigid snow storm went through this retirement community, icy streets and a cold sky with rows of houses and christmas decorations

Ocean Pines

4.5/5(5 area reviews)

Boasting the largest concentration of retirees on the Eastern Shore, this community offers the Ocean Pines Golf Club, designed by Robert Trent Jones, and 13 parks, including White Horse Park. Enjoy golfing, park visits, and a peaceful atmosphere.

Downtown Ocean City

If you're spending some time in Downtown Ocean City, Ripley's Believe It or Not! and Jolly Roger at the Pier are top sights worth seeing.

Midtown Ocean City

4.5/5(1,528 area reviews)

Midtown Ocean City is beloved for its stunning beaches. Take some time to explore sights in the area like Seacrets Distilling Company and Jolly Roger Amusement Park.

West Ocean City

4.5/5(902 area reviews)

Discover fishing charters, boating, and marinas in this census-designated area, located across the Sinepuxent Bay from Ocean City. Shop at Outlets Ocean City and easily access the beach resort town via the Harry W. Kelley Memorial Bridge.

Panoramic sunset over wetlands at Assateague Island in Maryland

Assateague Pointe

5/5(1 area review)

While Assateague Pointe isn't home to many top sights, Frontier Town Water Park and Golf and Ocean City Inlet are some notable places to visit nearby.

Sunset Island

While there might not be top attractions in Sunset Island, you can explore the larger area and discover places like Maui Golf and Seacrets Distilling Company.