The lifestyles and livelihoods of generations of watermen, shipbuilders and farmers have been shaped by a landscape that, even to this day, makes it easy for visitors to imagine 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.  Specially trained Chesapeake Bay Storytellers offer guided tours and authentic experiences both on and off the water. 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, a site on the NATIONAL UNDERGROUND RAILROAD NETWORK TO FREEDOM owing to the canal’s history as a maritime escape route for freedom seekers, captures the history of the 165-year-old waterway. Walk or bike along the Ben Cardin C&D Canal Trail to see the expansive waterway, stroll through natural areas and watch wildlife, and see massive container ships traveling the canal. Schedule a boat tour through Chesapeake Water Tours and watch the sunset paint the sky red.

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. Restored outbuildings, replica slave quarters and a tobacco barn on the grounds tell the story of Mount Harmon’s enslaved labor force.

Across the river is Georgetown, which the British burned during the War of 1812. It has been rebuilt and is now 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 vintage household equipment. Here too is the SASSAFRAS NATURAL RESOURCES MANAGEMENT AREA, popular for its trails and spectacular views of the Sassafras River and Chesapeake Bay from the high banks that face toward the South. The Knock's Folly Visitor Center features exhibits including those that highlight the history of the local Native American Tockwogh tribe.

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. Visit over Memorial Day weekend for the annual Chestertown Tea Party festival with a tea toss reenactment, colonial parade, block party, street performances, local fare and more. Get out on the water on the CAPTAIN JOHN SMITH NATIONAL HISTORIC TRAIL with the SULTANA EDUCATION FOUNDATION. Choose from themed, guided kayaking tours like “Oysters and Indians” or help unfurl the sails and steer the foundation’s replica 1768 merchant vessel as it navigates the Chester River.

Veer southwest 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, a remote island sanctuary for migratory waterfowl, is just to the south. It offers wildlife viewing platforms and extensive hiking and water trails. Make time for a self-guided auto tour of CHESAPEAKE FARMS, a 3,000-acre wildlife and agricultural research and demonstration area located on one of the largest conservation easements in Maryland to learn about sustainable agricultural practices and land conservation.

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.

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