2 Best Restaurants in Chestertown, The Eastern Shore

This relaxed, contemporary dining room has high, sloped ceilings and skylights. Among its crab offerings and pasta, as well as chops and steaks, the café's most sought-after entrée is baked rockfish, but don't overlook the oyster fritters, a signature dish. Weekend nights are busy, and the service here is genuine and attentive.

This is the place to mingle with C'town residents as well as with Washington College students and local pols, for good conversation—indoors or alfresco—over fresh coffee (including excellent espresso) or fine wine, by the glass or bottle, to accompany hearty, healthy soups, salads, and sandwiches. Friday night is "wine night" with complimentary hors d'oeuvres, often accompanied by live music. Wi-Fi's in the air here.