Don’t let its museum-like historic setting fool you—this Eastern Shore town knows how to throw a party. Residents celebrate year-round with a calendar of events ranging from a reenactment of the rebellious 1774 tea party, held every Memorial Day weekend, to arts and music festivals. In the rare instance there’s not something organized going on, you can still take in a play or concert at the Garfield Center for the Arts, explore the galleries and boutiques along High Street, or cruise aboard the River Packet, a 1920s-style yacht, or the Sultana, a reproduction 1768 schooner that gets feted at Downrigging Weekend at the end of October. Locals flock to Evergrain Bread Company (201-203 High St.; 410-778-3333) for the flaky croissants and tuck into cream-of-crab soup and rockfish dinners at Lemon Leaf Cafe (337 High St.; 443-282-0004).
Distance from DC: 80 miles.
Mark your calendar: Bring your kids—and wizard’s hat—to the Harry Potter Festival, October 2 and 3.