Situated on the Chester River, Chestertown, Maryland, is one of the most graciously pretty Eastern Shore towns. Impressive Revolutionary War-era buildings line the brick streets, shaded by huge trees. Spacious porches and old-fashioned gardens encircle multistory Victorian homes in this town 30 mi/50 km east of Baltimore.
Memorial Day weekend is when Chestertown residents re-enact the not-so-famous Chestertown Tea Party of 1774. Inspired by Boston's party five months earlier, the citizens of Chestertown staged their own uprising when the Geddes, carrying a small cargo of tea, docked in Chestertown.
Whenever you visit, take the walking tour (contact the Kent County Tourism Office for information). Allow several hours to see the sights, including the Geddes-Piper House, a circa-1700s home that also houses the Historical Museum of Kent County, and Washington College, one of the oldest in the U.S. If you're spending the night, consider staying at the restored White Swan Tavern.
Just southwest of Chestertown is the Eastern Neck Island National Wildlife Refuge, a preserve that attracts a variety of birds, including swans and bald eagles. The area attracts many cyclists to its congestion-free, scenic roadways.
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