Chestertown looks like a town that decided long ago what it wanted to be and then very sensibly never changed its mind. It sits on the Chester River on Maryland's Eastern Shore, at the head of navigation, and its old brick houses, many from the eighteenth century, still line the streets leading up from the waterfront. The place was a colonial port, shipping tobacco and grain to Europe, and the wealth that built those handsome Georgian merchants' homes is still visible in the cornices and doorways.
Two bits of history are worth knowing. In 1774, while Boston's tea party was making headlines, Chestertown's own citizens boarded a ship and threw its tea into the river in protest at the British tax, and the town re-enacts the event each May with a festival, costumed crowds and a mock trial. The other is Washington College, founded in 1782 with the personal backing of George Washington, who permitted use of his name and served on its board. It makes the town feel lively in term time, with students filling the cafes on High Street.
For a rider, the pleasure is the surrounding country. The Chesapeake Country byway runs across flat farmland and tidal creeks, with fields of corn, soybeans and wheat, old barns and white farmhouses, and long straight stretches interrupted by gentle bends. This is no corner-carving territory, and the speed limits are low and enforced, but it is calm, scenic riding that suits a warm afternoon. Watch for farm machinery, deer, and, at harvest time, mud and dust carried onto the road. Spring and early autumn are the best seasons; July and August are hot, humid and buzzing with insects.
Chestertown makes an easy rest. The population is about five thousand, so there is petrol, groceries and a decent choice of places to eat, including seafood with Chesapeake crab where it is in season. The waterfront park is a good place to sit and watch boats, and the schooner Sultana, a replica of an eighteenth-century vessel built here, is sometimes moored nearby.