The Top 14 Things to Do on Maryland's Eastern Shore (2024)

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See the Boats in Chesapeake City

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.

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Explore the History of Chestertown

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.

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Boat in One of the Many Marinas in Rock Hall

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.

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Enjoy Delicious Seafood and Drinks on Kent Island

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.

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Appreciate the Arts in Easton

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.

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Head to a Popular Museum In St. Michaels

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.

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Go Sports Fishing on Tilghman Island

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.

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Step Back in Time in Oxford

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.

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Birdwatch in Cambridge

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.

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Catch a Baseball Game in Salisbury

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.

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Hit the Beach in Ocean City

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 amusem*nt 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.

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Spot Wild Ponies at Assateague Island National Seashore

Assateague Island is most known for the more than 300wild ponieswho 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.

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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 annualNational 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.

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Take the Ferry to Smith Island

Maryland's only inhabited off-shore island on the Chesapeake Bay is accessible by ferry only, fromPoint Lookoutor 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.