The Maryland Eastern Shore, a captivating peninsula stretching for hundreds of miles between the expansive Chesapeake Bay and the rhythmic Atlantic Ocean, is a haven of recreational opportunities and a cherished summer vacation destination. This alluring region beckons visitors from far and wide, drawing them in with its tapestry of historic towns, sun-kissed beaches, and breathtaking natural landscapes. Here, the possibilities for adventure are as vast as the horizon itself.
From the gentle lapping of waves against a sailboat to the thrill of reeling in a prized fish, the Maryland Eastern Shore offers an array of activities to suit every taste. Boating enthusiasts can navigate the intricate waterways, while swimmers can revel in the refreshing embrace of the ocean. Anglers can cast their lines in pursuit of the region’s abundant marine life, while bird watchers can train their binoculars on the diverse avian species that call this peninsula home. Cyclists can explore the scenic backroads, and golfers can tee off amidst verdant fairways.
Adding to the allure of the Maryland Eastern Shore are the vibrant annual events that enliven its charming resort communities. Waterfront festivals celebrate the region’s maritime heritage, while seafood festivals tantalize taste buds with the freshest catches of the day. Boating regattas and races showcase the skill and precision of sailors, while fishing tournaments test the mettle of anglers. Boat shows display the latest in nautical innovation, while museum events delve into the region’s rich history and culture. Arts and crafts shows offer a glimpse into the creative spirit of the Eastern Shore, showcasing the talents of local artisans.
This guide serves as your compass, highlighting the very best that the Maryland Eastern Shore has to offer. From basking in the sun on pristine beaches to experiencing the thrill of a baseball game, prepare to embark on an unforgettable journey through this beautiful corner of Maryland.
1. See the Boats in Chesapeake City
Nestled at the northern tip of the Eastern Shore, Chesapeake City exudes a captivating small-town charm. Its defining feature is the unparalleled views it offers of majestic ocean-going vessels gliding along the Chesapeake & Delaware Canal. This historic waterway, stretching for 14 miles, dates back to 1829 and serves as a vital link between the Chesapeake Bay and the Delaware River. History buffs can delve into the canal’s fascinating past at the C&D Canal Museum, which chronicles its construction, operation, and impact on the region.
Beyond its maritime allure, Chesapeake City boasts a vibrant arts scene, with galleries showcasing the works of local and regional artists. Antique shops beckon treasure hunters with their eclectic collections of vintage finds. Outdoor concerts fill the air with music during the warmer months, while boat tours offer a unique perspective of the town and its surrounding waters. Horse farm tours provide a glimpse into the region’s equestrian heritage, and seasonal events add a touch of festive cheer throughout the year. A variety of excellent restaurants and cozy bed-and-breakfasts ensure that visitors are well-fed and comfortably accommodated.
2. Explore the History of Chestertown
Step back in time in Chestertown, a historic town gracefully situated on the banks of the Chester River. In its early days, Chestertown served as a vital port of entry for settlers arriving in Maryland, playing a crucial role in the region’s development. Today, the town is a living museum, showcasing meticulously restored colonial homes, stately churches, and a delightful array of shops.
The Schooner Sultana offers an immersive experience, allowing students and adult groups to sail the Chesapeake Bay and learn about its rich history and delicate environment. Monument Park, a designated Civil War trail site, invites visitors to stroll amidst monuments that stand as silent witnesses to the tumultuous era. Chestertown is also proud home to Washington College, the tenth oldest college in the United States, adding to the town’s intellectual and cultural vibrancy.
3. Boat in One of the Many Marinas in Rock Hall
Rock Hall, a quaint fishing town on the Eastern Shore, has earned its reputation as a boater’s paradise, boasting an impressive 15 marinas. Whether you’re a seasoned sailor or a novice navigator, Rock Hall provides the perfect launching point for your Chesapeake Bay adventures.
Even if you’re not on the water, Rock Hall offers a variety of attractions to keep you entertained. The Waterman’s Museum provides a fascinating glimpse into the lives and traditions of the region’s watermen, with exhibits showcasing the tools and techniques used in crabbing, oystering, and fishing. For nature enthusiasts, the Eastern Neck National Wildlife Refuge is a must-visit destination. This protected area is home to 234 species of birds, including majestic nesting bald eagles. Hiking trails wind through the refuge, leading to an observation tower that offers panoramic views of the surrounding landscape. Picnic tables provide the perfect setting for a relaxing lunch, while public fishing areas and a boat launch cater to anglers and boaters.
4. Enjoy Delicious Seafood and Drinks on Kent Island
Kent Island, aptly named "Maryland’s Gateway to the Eastern Shore," is strategically located at the base of the Chesapeake Bay Bridge. Its convenient proximity to the Annapolis/Baltimore-Washington corridor has fueled its rapid growth, making it a popular destination for both residents and visitors.
Kent Island is a culinary haven, with an abundance of seafood restaurants serving up the freshest catches of the day. Marinas dot the coastline, providing ample opportunities for boating and water sports. Outlet stores offer a tempting array of shopping options. Be sure to make a stop at one of the island’s distilleries and wineries, where you can sample locally produced spirits and wines. Blackwater Distillery, for example, has garnered acclaim for its Sloop Betty Vodka, which earned a gold medal for Best Vodka in Show at the New York Wine & Spirits Competition.
5. Appreciate the Arts in Easton
Easton, conveniently situated along Route 50 between Annapolis and Ocean City, is a charming town that invites visitors to pause and appreciate its artistic and cultural offerings. Recognized as one of the "100 Best Small Towns in America," Easton boasts a historic ambiance and a thriving arts scene.
Antique shops beckon treasure hunters with their unique finds, while the Avalon Theater, an art deco performing arts venue, hosts a variety of performances throughout the year. The Pickering Creek Audubon Center provides a sanctuary for nature lovers, with trails and educational programs that promote environmental awareness. If you’re visiting in July, don’t miss the Plein Air Easton Art Festival, the largest juried plein air (outdoor) painting competition in the United States. The Academy Art Museum, with its impressive collection of over 1,400 works, is a testament to Easton’s commitment to the arts.
6. Head to a Popular Museum In St. Michaels
St. Michaels, a quaint historic town, is a beloved destination for boaters, drawn to its small-town charm and its array of gift shops, restaurants, inns, and bed and breakfasts. The town’s main attraction is the Chesapeake Bay Maritime Museum, an 18-acre waterfront museum that celebrates the region’s maritime heritage. The museum’s exhibits showcase Chesapeake Bay artifacts and offer programs that delve into maritime history and culture. With nine buildings and an extensive collection of sail, power, and rowboats, the museum provides a comprehensive overview of the region’s seafaring past. St. Michaels is also renowned for its sailing, bicycling, and, of course, its delectable freshly-caught crabs and oysters.
7. Go Sports Fishing on Tilghman Island
Tilghman Island, nestled between the Chesapeake Bay and the Choptank River, is a haven for sports fishing enthusiasts and seafood aficionados. Accessible by a drawbridge, the island boasts several marinas, some of which offer charter cruises for those seeking to explore the surrounding waters.
Tilghman Island is home to the Chesapeake Bay Skipjacks, the only commercial sailing fleet in North America, a testament to the region’s enduring maritime traditions. For nature lovers, the island offers a variety of opportunities to connect with the outdoors. Rent a bike and explore the scenic backroads, charter a boat for a fishing expedition, or rent a kayak or paddleboard and glide along the tranquil waters.
8. Step Back in Time in Oxford
Oxford, the oldest town on the Eastern Shore, exudes a timeless charm that transports visitors back to Colonial times. Once a bustling port of entry for British trade vessels, Oxford retains its nautical character, with several marinas catering to boating enthusiasts.
Beyond its maritime appeal, Oxford offers a glimpse into the region’s rich history. The Robert Morris Inn, one of the oldest inns in America, stands as a testament to the town’s enduring legacy. The Oxford-Bellevue Ferry, operating for over 339 years, provides a scenic and historic passage across the Tred Avon River.
9. Birdwatch in Cambridge
Cambridge, a vibrant town on the Eastern Shore, is home to the Blackwater National Wildlife Refuge, a sprawling 27,000-acre sanctuary for migrating waterfowl. This protected area provides a vital resting and feeding ground for a diverse array of species, including 250 species of birds, 35 species of reptiles and amphibians, 165 species of threatened and endangered plants, and numerous mammals.
For those seeking luxurious accommodations, the Hyatt Regency Resort, Spa, and Marina, a renowned romantic getaway destination, sits majestically on the Chesapeake Bay. The resort features its own secluded beach, an 18-hole championship golf course, and a 150-slip marina.
10. Catch a Baseball Game in Salisbury
Salisbury, the largest city on the Eastern Shore, offers a vibrant urban experience amidst the region’s natural beauty. Catch a game at Arthur W. Perdue Stadium, home to the minor-league Delmarva Shorebirds, and cheer on the future stars of baseball.
Before or after the game, visit the Eastern Shore Baseball Hall of Fame to learn about baseball legends, such as Frank "Home Run" Baker. The Salisbury Zoological Park offers a delightful escape into the animal kingdom, while the Ward Museum of Wildfowl Art houses the most extensive collection of bird carvings in the world.
11. Hit the Beach in Ocean City
Ocean City, Maryland, boasts 10 miles of pristine white sand beaches along the Atlantic Ocean, making it the perfect destination for swimming, surfing, kite flying, sandcastle building, and leisurely strolls. This bustling beach town offers a plethora of attractions, including amusement parks, arcades, miniature golf courses, shopping malls, an outlet shopping center, movie theaters, go-kart tracks, and the iconic 3-mile Ocean City Boardwalk. With a wide range of accommodations, restaurants, and nightclubs, Ocean City caters to a diverse range of vacationers.
12. Spot Wild Ponies at Assateague Island National Seashore
Assateague Island, famed for its population of over 300 wild ponies, offers a unique and unforgettable experience. These majestic creatures roam freely along the beaches, adding a touch of untamed beauty to the landscape.
As a national park, Assateague Island allows camping, providing an immersive experience in nature. Hotel accommodations can be found in nearby Ocean City, Maryland, or Chincoteague Island, Virginia. Assateague Island is also a haven for bird watching, seashell collecting, clamming, swimming, surf fishing, and beach hiking.
13. Eat Blue Crab in Crisfield
Crisfield, located at the southern end of the Maryland Eastern Shore, is known as "The Crab Capital of the World." This charming town is home to numerous seafood restaurants, serving up the freshest and most delectable blue crab dishes.
Crisfield also hosts the annual National Hard Crab Derby, a celebration of the region’s most iconic crustacean. The Somers Cove Marina, one of the largest marinas on the East Coast, provides a haven for boating enthusiasts. Nature lovers can explore the numerous trails that wind through the surrounding landscape, offering opportunities for walking and biking.
14. Take the Ferry to Smith Island
Smith Island, Maryland’s only inhabited off-shore island on the Chesapeake Bay, offers a unique glimpse into a bygone era. Accessible only by ferry from Point Lookout or Crisfield, this small island is home to approximately 200 permanent residents.
The island’s isolation has preserved its colonial heritage, with residents speaking a dialect of English that closely resembles that of the 17th century. Smith Island is also the birthplace of Maryland’s state dessert, the Smith Island Cake, a multi-layered confection that is as delicious as it is iconic. With a few bed and breakfasts, the Smith Island Museum, and a small marina, Smith Island provides a truly unique getaway experience.
