A stopping place for travelers since colonial days, when it was a prime Chesapeake port,
CHESTERTOWN
is the northernmost town on the eastern shore. Stretching west along High Street from the Chester River, it is surprisingly intact, with its fine old riverfront homes, a courthouse square lined with ornate wooden cottages, and a generally languorous feel that makes it a popular weekend escape from Baltimore or DC. Many of the old houses, like the
Widow's Walk Inn
, 402 High St (tel 410/778-6455 or 1-888/778-6455,
; $75-100), have been converted into
B&Bs
, while others now house top-rated
restaurants
like the
Feast of Reason
, 203 High St (tel 410/778-3828; closed Sun), and the
Imperial Hotel
(tel 410/778-5000) across the street, with its swanky dining room. The
visitor center
, 400 S Cross St (Mon-Fri 9am-4pm, Sat 10am-2pm; tel 410/778-0416), has information about walking and cycling tours.
To the west of town, fifteen miles of country lanes lead down to the wharves and dockside restaurants of
ROCK HALL
, an old fishing port where you can watch the day's catch being unloaded while chewing on crab legs at the bare-bones
Waterman's Crabhouse
(tel 410/778-1803) on the main pier. The
Chesapeake Flyer
catamaran service lands here, and bikes can be rented from the marina office.
