Things to do in Eastern Shore
Explore thousands of activities with free cancellation and no added fees.
Design your experience with airport transfers, excursions, day tours & more.
Get an insider's look in what to book before you travel.
Most popular experiences in Eastern Shore
Tours & day trips
See all 60 activitiesOpens in new tab
Bethany Beach Blitz Scavenger Hunt
Water activities
See all 23 activitiesOpens in new tab
Kayak Tour along Assateague & Chincoteague Island, Virginia
History & culture
See all 12 activitiesOpens in new tab
Half Day Private Bus Tour of Annapolis Up to 13 people
Adventure & outdoor
See all 3 activitiesOpens in new tab
Assateague Island: Bike Rental from the Bayside Stand
Popular places to visit
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.
U.S. Naval Academy
See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.
Jolly Roger Amusement Park
Bring your family to Jolly Roger Amusement Park and enjoy this exciting theme park in Ocean City. Amble around this family-friendly area's seaside or seek out the golf courses.
Longwood Gardens
Explore the great outdoors at Longwood Gardens, a lovely green space in Kennett Square. Stroll along the riverfront or visit the shops in this family-friendly area.
Maryland Beach
Why not spend a care-free afternoon at Maryland Beach during your travels in Ocean City? Stroll along the seaside in this family-friendly area or visit its lively bars.
Roland E. Powell Convention Center
Learn about the events happening in Roland E. Powell Convention Center during your trip to Ocean City. Stroll along the beautiful beaches or discover the breathtaking sunrises in this family-friendly area.
Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
Frontier Town Water Park and Golf
Bring your family to Frontier Town Water Park and Golf and enjoy some excitement at this theme park in Berlin. Stroll along the beautiful beaches in this family-friendly area or seek out the golf courses.
Areas of Eastern Shore
North Ocean City
A noteworthy feature of North Ocean City is its stunning beaches. While you're in town, be sure to stop and check out Ocean City Beach and Carousel Ice Skating Rink.
Downtown Ocean City
If you're spending some time in Downtown Ocean City, Ocean City Beach and Jolly Roger at the Pier are top sights worth seeing.
Midtown Ocean City
Midtown Ocean City is known for its stunning beaches, and with sights like Ocean City Beach and Seacrets Distilling Company, you won't get bored spending a day wandering around this part of Ocean City.
Ocean Pines
You'll enjoy the beaches and live music in Ocean Pines. You might want to make time for a stop at Ocean Pines Golf and Country Club or River Run Golf Club.
West Ocean City
The beaches and seaside views are top of the list for many visitors to West Ocean City. A stop by Tanger Outlet Center or Ocean City Harbor might round out your trip.
Sunset Island
While Sunset Island may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Seacrets Distilling Company and Ocean Plaza Mall Shopping Center.
