48 miles NE of Annapolis; 55 miles E of Baltimore; 70 miles NE of Washington, D.C.; 50 miles SW of Wilmington
Chestertown, north of the Bay Bridge, looks terrific for a town her age. Built in 1706 on the Chester River, this was once a thriving seaport. Residents here showed their revolutionary leanings when they tossed English tea into the harbor, just as Boston's patriots did. The sea captains' homes, many built in the mid-1700s, still line Water Street -- an elegant sight as you cross the Chester River Bridge. As you cross, look for the yellow reproduction of the schooner Sultana. Chestertown also is home to Washington College, known for the Sophie Kerr Prize, a large cash award given to a graduating writing student each year. This picturesque riverside town makes for a good day trip or a leisurely weekend visit.