Hotels in Chestertown

Cobblestone streets wind past Federal-era mansions in this Chesapeake Bay gem where history feels less like a museum and more like a neighbor who won't stop talking. The Chester River waterfront invites sailing adventures aboard traditional skipjacks, while Washington College students add youthful energy to the centuries-old town. High Street's galleries showcase local artists who've captured the distinctive Eastern Shore light. The Garfield Center for the Arts occupies a lovingly restored 1920s theater where performances continue in a space that's seen everything from vaudeville to indie films. Don't miss First Fridays when galleries stay open late and locals debate whether the best crab cakes come from waterfront restaurants or roadside shacks.