Take a break to see farm country, historic towns, nature preserves, good walking, authentic soda fountain, Bald Eagles, and the endangered Delmarva Fox Squirrel.
A drive along the upper eastern shore of Maryland will take you through historic towns, nature preserves and farm country; you will never once be far from the water. Begin your trip on Route 213 in Chesapeake City at the western end of the Delaware Canal and Chesapeake. As you head south, this is one drive where there are many opportunities to walk along the way as you visit some interesting tourist spots. A way to begin the trip, in fact, is with a visit to the Canal Museum, where you can learn about how the place grew in the 1830s as a result of canal-related industries.
A walk through Chesapeake City’s historic district will further steep you in history. The 19th Century will come alive in these well-preserved antique houses and shops. Pass through Fredericktown and go across the Sassafras River to Kent County and the historic town of Georgetown. You’ll see the two brick houses that were spared from the British during the War of 1812 when Kitty Knight refused to leave, declaring, “If you burn this house, you’ll burn me with it.” The road continues through rolling farmland to Chestertown. Start at the Kent County Visitor Center and take a self-guided walking tour to view the courthouse, the Georgian homes, and the Emmanuel Episcopal Church with its Tiffany window. There are also plenty of antique stores, shops, and galleries.
For inherent beauty, take Chestertown’s High Street, Route 20, to Rock Hall, a bayside community formed by maritime trade. With fifteen marinas, this town is the pleasure boating capital of the upper shore. If you’re not interested to pursue a water adventure, take pleasure with the fruits of the sea at one of the many seafood restaurants. You may also opt to just visit the Rock Hall Museum and an old fashioned drugstore with an authentic soda fountain, both on Main Street. Head south out of town on Main Street, which becomes Route 445 to the Eastern Neck Wildlife Refuge, an island ecosystem with plenty of wildlife and extensive hiking trails, including Bald Eagles, more than 240 unique species of birds and waterfowl, and the endangered Delmarva Fox Squirrel.
Return to Route 213, you will drive through the picturesque Queen Anne’s County to Centreville, the county capital. South of Centreville, get on to Route 18 and head toward Kent Narrows, a waterfront village bustling with recreation and maritime industry. The town was settled in 1631 when a Virginian established a trading post here 3 years before settlers set up the colony of Maryland. Next, cross U.S. 50 to Stevensville, an 1850s village that is largely unchanged from its early days with 100 preserved edifices in its ancient district. Continuing west on U.S. 50, you will cross the Bay Bridge, the gateway linking the eastern and western shores.
Starting Point:
Chesapeake City, MD
Distance of Drive:
68 miles
Must Eat:
Fisherman’s Inn
3116 Main St. Grasonville, MD 31638
(on Route 50 just before Bay Bridge)
Phone: 410-827-8807
Call ahead to confirm hours of operation.
Good Stop For: Seafood
Best Time of Year for Drive:
Spring to fall
Points of Interest on Drive:
Rock Hall Museum E
Sandstone Falls
Eastern Neck Wildlife Refuge
Tagged with: best time:spring and fall • Maryland
Filed under: Best Road Trips