Strung like a collection of gems along a necklace of green fields and the blue waters of the Chesapeake Bay, the historic towns and quaint villages of Maryland’s Eastern Shore are filled with antique treasures, unique boutiques, charming cafés and inns, market stands bursting with local produce, and museums and marinas large and small. All are an easy drive just over the Delaware line.
Maryland has designated 18 routes throughout the state called Scenic Byways, and three are on the Eastern Shore. One of those, Scenic Byway Route 16, takes you through Chesapeake Country, beginning at Chesapeake City and extending 419 miles to Crisfield in the lower bay region. (A free guidebook of all of Maryland’s Scenic Byways, complete with maps and area highlights, are available at all visitors centers and town halls in the state, or by visiting visitmaryland.org/pages/byways.aspx.)
Part of the Chesapeake Country route takes you through the upper Chesapeake region, including the towns of Chesapeake City, Chestertown and Easton. Planning a day trip to visit these three towns is a good way to begin exploring the region.
Start from state U.S. 40 or Interstate 95 and head west toward Elkton in Cecil County. Turn south on Md. 213. Travel about seven miles to the bridge that spans the Chesapeake & Delaware (also known as the C&D) Canal. At its base lies the historic town of Chesapeake City.