Go here: Surrounded by farmland on one side and the Chester River on the other, Chestertown is a look back in time to the flourishing Colonial port it was in the 1640s, when it harbored vessels bound for Europe, the Caribbean and West Africa. The town's population today is barely larger than during the American Revolution, and the people of Chestertown still go about their lives on quiet cobblestone streets amid restored 18th-century houses and churches. The layout of the town, also the county seat of Kent County, is much the same as it was in Colonial times, encompassing dozens of historic structures, as well as newer antique shops, art galleries, restaurants and bars. During the Revolution, Chestertown merchants led protests against British rule, and each year the citizens of Chestertown commemorate their role in the war with the Chestertown Tea Party Festival, a long weekend of tours, parades, Colonial costumes and more.
Stay here: Brampton Bed and Breakfast Inn, 25227 Chestertown Road, 866-305-1860 or 410-778-1860; bramptoninn.com. In 2006, American Historic Inns and its companion Web site, iLoveInns.com, ranked the Chestertown B&B as one of the Top 10 romantic inns in the country and as "the ultimate in romantic travel." The Greek Italianate Revival manor house is a stunning -- and huge -- antebellum dwelling. Everything about it is writ large: the wraparound porch and, inside, a carved three-story staircase flanked by an enormous parlor and a dining area set with individual tables. Brampton, listed on the National Register of Historic Places, sits on 25 wooded acres. There are red buds, flowering crab apples, holly trees, dogwoods, poplars, loblolly pines and 1,800 exotic paulownias, a Chinese tree with large -- what else? -- heart-shaped leaves and violet flowers. Rates start at about $125 per night.
Eat here: The Fish Whistle, 98 Cannon St., 410-778-3566. Located at the end of Cannon Street, directly on the banks of the Chester River, The Fish Whistle is a great place for waterfront dining. Inside, the restaurant, known for its oysters and crab cakes, is a bright mix of mango- and lime-colored walls and blond wood, and guests at the bar or in the dining room still have a view of the water. The Fish Whistle has lunch and dinner hours every day and a bar menu available until midnight, with live music in the bar on Thursday nights. Boaters can dock for free at the Chestertown Marina if they call ahead. Dinner entrees range from abouot $12 to $25.
Don't miss this: Andy's, 3371/2 High St., 410-778-6779; andys-ctown.com. Andy's is a popular restaurant/bar/lounge hybrid that combines an intimate setting of four-person tables and white Christmas lights in one room, and a random assortment of old-fashioned easy chairs in another. It also has a game room with darts, trivia and pinball machines and a foosball table.
For daytime group entertainment, book a fishing trip or photography tour with Daddy's Girl Charters and Guide Service (daddysgirlcharters.com). Fish the Chesapeake Bay and the harbor of Rock Hall for rockfish, stripers, perch, catfish, hardheads, spot and bluefish. Tackle and licensing provided by the Captain. Or see a show at the Prince Theatre (210 High St. Box office: 410-810-2060) performed by a variety of community groups and local artists, as well as student groups from Washington College.
Get there: Chestertown is about 70 miles from Baltimore -- about a 90-minute drive. From the Bay Bridge, take U.S. 50 east to the U.S. 50/301 split. Continue north on U.S. 301. Exit on Route 213 North toward Centreville. Continue on 213 across the Chester River Bridge, then turn left at Route 291 West.
For more information: Call 410-778-0500 or go to chestertown.com.