6 Best Restaurants in Annapolis and Southern Maryland, Maryland

In what was once a hardware store, this casual eatery has one interior wall of exposed brick and another of exposed plaster; both are used to hang art for sale by local artists. Daily specials are chalked on a blackboard and include a large cheese-and-pâté plate, flatbread pizzas, deli sandwiches, espresso, waffles, soups, and salads.

Deli sandwiches (many named after local politicians), burgers, subs, crab cakes, and milkshakes are the fare at this very busy counter-and-booth institution. Baltimoreans Ruth and Chick Levitt purchased the building, built in 1899, in 1965. Their son Ted and his wife, Beth, continue the business today. Don't plan on placing an order at 8:30 am on a weekday or 9:30 am on a weekend—that's when the place stops to say the Pledge of Allegiance.

One of the few restaurants in the city with a rooftop, this establishment co-owned by Annapolis mayor Gavin Buckley takes full advantage of its lovely perch and features live music most evenings. The menu satisfies global palates in a town otherwise known for Old Bay and crab cakes, bringing in a bit of Australian flair from the mayor's homeland.

Modest Neptune's claims of preparing "the world's best mussels" rings true with many, making the trip to this tiny town just north of Chesapeake Beach worthwhile. Attached to the small bar, a glass-enclosed dining room with a brick floor is a friendly, informal spot to dig in to its signature dish—it's also a great place for nice views. Also on the menu are seafood pastas, burgers, and cuts of Angus beef. Don't let the "divey" atmosphere dissuade you; order the mussels (sold by the pound) and enjoy. This is the best restaurant (and there are few choices) in town.

This traditional English-style pub serves better-than-usual tavern fare, as well as more than 100 beers—30 on tap—including five Fordham beers and others from around the world. Brunch is served on Sunday, and nationally known folk, rock, jazz, country, and bluegrass artists perform most nights.