6 Best Restaurants in The Eastern Shore, Maryland

Unobtrusively situated on St. Michaels' busy main street, 208 Talbot, long a favorite among discriminating diners, has several intimate dining rooms with exposed brick walls and brick floors. Specialties include such original first-course dishes as house-cured gravlax served with fresh mango, avocado, jalapeño pesto, and grilled flat bread; and more-traditional second-course entrées such as whole grilled rockfish accompanied by braised greens, grape tomato relish, and hush puppies; as well as a welcome variety of meat dishes. Small plates ($8–$14) are available for more conservative appetites, and on Saturday there's a four-course prix-fixe menu available ($55).

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.

Owned and operated by the same family since 1965, this St. Michaels landmark started as a clam- and oyster-shucking house for watermen long before that. Diners at both indoor and outdoor tables have panoramic views over the harbor to the river beyond, but dockside tables are the best. As the name suggests, this is the down-home place for fresh steamed and seasoned blue crabs. But the extensive menu also includes sandwiches and other light fare as well as other seafood and meat dishes. Children's platters are available, too.

A whimsical red, white, and green color scheme; painted vines climbing the walls; and polished wooden floors distinguish this bistro. Weather permitting, you can eat outdoors at wrought-iron tables in a brick courtyard. The creative and diverse menu changes twice a month, with such dishes offered as veal fettuccine Montrachet topped with goat cheese and a tomato cream sauce, and sauté of seafood including lobster, shrimp, and scallops.

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.

Housed inside a brilliantly converted theater, with its stage area is retained and periodically used for a variety of presentations, this eclectic eatery is well worth a meal, from vegetable risotto and jerk pork plate to, of course, crab cakes. Allow some extra time to wander the upper-level art gallery, its works all for sale. And you might luck into one of the periodic screenings of Runaway Bride. Sunday brunch and weekend dinners are popular with locals. On the weekends the stage has live entertainment.