Set along one of the busiest shipping canals in the world, Chesapeake City has roots in the early 1800s, when the 17-mile canal was built to allow ships to pass from the Delaware River to the Chesapeake Bay by a quicker route. Many of the original Victorian buildings remain, and are today used as residences, inns and retail shops. Stop into town hall on Bohemia Avenue and pick up a map with the locations of businesses and recreational areas, which includes the C&D Canal Museum.
The town is split in two, a north and a south side at either end of the canal bridge (a free water taxi runs between the two sides from April to October). The southern side, which contains the majority of the shops, eateries and inns, is entirely walkable. Public places include an exceptional municipal dock—quite popular with boaters transiting the canal—and a boardwalk, which is used for a number of public festivals and boasted the area’s only outdoor skating rink last winter.
Town-wide activities throughout the year include a St. Patrick’s Day parade, Independence Day celebration, and in the fall and winter, an annual Ghost Walk,
Winterfest, Candlelight House Tour and two 5K walk/runs, plus Murder Mysteries held at a local inn, the Blue Max.
Paintings of local scenes and wildlife and other works by local artisans are everywhere, including Town Hall and many of the shops along Bohemia and George streets.
Highlights not to miss:
Make sure you also visit the C&D Canal Museum before you head out of town. It details in words, pictures and interactive displays the fascinating history of the building of the canal, which once included a series of steam-driven locks for ship passage.
Continue on Md. 213 south for 16 miles and you’ll arrive at Georgetown in Kent County, right on the banks of the Sassafras River. It is home to the War of 1812-era Kitty Knight Historic House and Inn, which also houses a restaurant. In addition to marina facilities, this small village has several eateries, gift and marine stores, plus a small public swimming beach. If you want to spend a day on the river or the Chesapeake, consider a cruise on an authentic fishing and crabbing boat through Capt. John’s Sassafras Adventures.
Travel south a few miles to Galena, which offers several antiques shops, and make a right at the light on Cross Street continuing on Md. 213 toward Chestertown, which is about 15 miles away. But consider a side trip off Md. 213 to one of the best public swimming beaches on the Chesapeake. Take a right onto Md. 298 and follow the signs to Betterton.
During the past two centuries, the beach was, and continues to be, popular with those escaping the summer heat of Baltimore. Bathers once arrived by sail and steamboat—and now by car—to enjoy the cooling breezes off the bay. The waterfront area includes a lovely public park with a pavilion and a small marina, and it is open year-round. Take a lunch and watch the ships pass by.