7 Spectacular Places to Cycle on Maryland's Eastern Shore

Assateague Island
Assateague Island | © Jim Pennucci / Flickr
Photo of Kristina Gaddy
3 May 2018

With flat land and lots of small roads, Maryland’s Eastern Shore between the Chesapeake Bay and the Atlantic Ocean is the perfect place to find day or weekend-long biking trips. Here are seven great places to bike on Maryland’s Eastern Shore.

Kent Island Bike Trails

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Sunset at Crab Alley Creek | Sunset at Crab Alley Creek

The Cross Island Trail on Kent Island is perfect for a half-day bike ride. Kent Island is right across the Chesapeake Bay Bridge, and the trail runs 5 miles (8 km) from the Terrapin Nature Park to Ferry Point Park. If you feel like a longer ride, you can bike another 6 miles (10 km) south to the southern end of the island. There are also two spurs from the main trail at the northern and southern ends of the island, and in total, you can bike 28 miles (45 km) all with spectacular views of the Chesapeake Bay. While you’re on Kent Island, check out some of the great seafood restaurants in Kent Narrows.

Blackwater National Wildlife Refuge

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Blackwater National Wildlife Refuge - East Side | Blackwater National Wildlife Refuge - East Side

The Blackwater National Wildlife Refuge near Cambridge, Maryland protects the wildlife habitat on the Eastern Shore. They have two paved bike loops on the refuge that are approximately 4 and 7 miles (6.5 and 11 km) long. The visitor center also offers maps for longer routes on local roads that take riders through the refuge and surrounding area. As you ride, keep an eye out for the Delmarva Fox Squirrel and Bald Eagles, species that call the wildlife refuge home.

Harriet Tubman Underground Railroad Visitor Center and State Park

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Located close to the Blackwater National Wildlife Refuge, the newly opened Harriet Tubman Underground Railroad Visitor Center is also a great place to start a bike trip. Many of the locations on the Harriet Tubman Underground Railroad Trail are close by and bikeable. Multimedia exhibits inside the visitor center share the story of Harriet Tubman’s life on the Eastern Shore, and as you bike around the area, you’ll be seeing a landscape that remains similar to what Tubman saw as a young enslaved woman.

The Oxford-Easton Loop

North of the Blackwater National Wildlife Refuge are the towns of Oxford, Maryland and Easton, Maryland, and the roads in between make a great loop for biking. There are a number of bike outfitters in the area where you can rent a bike if you’re in the area and don’t have one of your own. From Easton, you can bike south on state route 333 to Oxford, where you’ll have to take a ferry ride across the narrow Tred Avon River. Then you bike north and can go farther west to the town of St. Michaels and check out the great seafood restaurants for lunch, or head back east to Easton. If you include the St. Michaels stop, the loop is 30 miles (48 km).

Pocomoke City

Near Pocomoke City right in the center of the Delmarva peninsula is where you’ll find some good trail riding. Since the Eastern Shore is very flat, we can’t quite call it mountain biking, but it’s not road biking.

Pocomoke River State Park

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The Pocomoke River State Park is located inside the Pocomoke State Forest. The park has multi-use trails, including mountain biking trails. You can make a whole weekend of hanging out at the park, since they have campsites, plus a pool and nature center.

Ocean City, Maryland

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Get up early and hit the boardwalk in Ocean City, Maryland for a great view of the Atlantic Ocean. During the summer months when the boardwalk gets crowded, you’re only allowed to bike on the 3-mile-long (5 km) boardwalk until 11 a.m. There are lots of places to stop along the way, such as the famous Thrasher’s French Fries. If you’re looking for a longer ride, bike north along Atlantic Avenue. You can even bike to the Delaware beaches, but state route 528 has heavier traffic so be aware of your surroundings.


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Assateague State Park

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If you are feeling very adventurous, you can bike the 12 miles (19 km) from Ocean City south to Assateague Island. Assateague State Park is also a great place to visit on its own. Known for the wild ponies who roam Assateague and Chincoteague, the park is packed with visitors in the summer. Here, you can bike on park roads that are not heavily trafficked and explore the island and beaches. The park also offers places to canoe and kayak, and camping along the beach (reservations are recommended).