The lifestyles and livelihoods of generations of watermen, shipbuilders and farmers have been shaped by an unspoiled landscape that, even to this day, makes it easy for visitors to imagine earlier times when goods were shipped to “faraway Baltimore” in wooden barrels lashed aboard schooners. The pace of life is slower here. Charming small towns are often accessed by boat as well as car. Popular pursuits include biking, kayaking, enjoying the cultural scene in arts communities and dining on some of the nation’s best seafood. Travel this byway to explore the Great Chesapeake Bay Loop, your key to Chesapeake adventures.
Upper Eastern Shore section from Chesapeake City to Kent Island
Including MD 213 & MD 18
From Chesapeake City, you can look out over the 14-mile-long Chesapeake and Delaware Canal to see modern-day ships dwarfing Victorian homes and shops along the banks. The C&D Canal Museum captures the history of the 165-year-old waterway. Walk or bike along the Ben Cardin C&D Canal Trail, to experience scenic views and the natural history of the area.
Head south along winding roads that lead past spectacular scenery. Then, as you enter Cecilton, plan a stop at Crystal Beach, a summer town on the Elk River that is popular with swimmers and anglers. Nearby is the Stemmers Run Managed Hunting Area, which, outside of hunting season, is known for its hiking and fishing.
A side trip reveals the graceful beauty of Mount Harmon Plantation in Earleville. This 200-acre Colonial plantation, featuring an antiques-filled manor house museum and walking trails, is on a peninsula surrounded by the Sassafras River.
Across the river is Georgetown, which the British burned during the War of 1812 but has been rebuilt and is a popular place for dining and entertainment. Continue toward Galena and on to Kennedyville, where you will find Crow Farm Vineyard and Winery. Stop at the Kent Museum to see displays of antique tractors, horse-drawn sleds and household equipment.
Sidetrack to the town of Betterton, a beach resort that still boasts fine examples of Victorian-era architecture. Back on the byway, farms glide by as you head to Chestertown, a Colonial port and National Historic Landmark, which is home to Washington College, founded in 1782 and named for its patron, George Washington. Among the elegant brick town homes in the city’s historic district you can enjoy concerts in the square. Get out on the water on the Captain John Smith National Historic Trail with a paddling or sailing tour led by the Sultana Education Foundation.
Veer west to Rock Hall, which has more than a dozen marinas offering mooring and charter services. The town also prides itself on excellent seafood dining, a homemade ice cream shop and a small, maritime-oriented museum. The Eastern Neck National Wildlife Refuge, an isolated ecosystem with nesting bald eagles and extensive hiking trails, is just to the south.
The area that extends from Chestertown through Centreville and into Queenstown is famous for its large number of fine antiques shops. But you can also find bargains on name-brand items at Premium Outlets. Along the way, make a stop at the Museum of Eastern Shore Life to admire an eclectic collection of artifacts ranging from a log canoe to early hand tools.
Grasonville invites you to get back to nature at the Chesapeake Bay Environmental Center surrounded by prime hiking, canoeing and birdwatching trails. Then stretch your legs some more after crossing over to Kent Island, where the Cross Island Trail extends for six miles from Terrapin Nature Park to the Kent Narrows.