5 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.

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.

Jars of pickled chard stems and radishes, preserved lemons, and pepper jelly line the shelves at this lively spot on Main Street run by a husband-and-wife team who both have impressive culinary resumés and a shared passion for pickling, fermenting, and preserving. The chef's roots in the Pennsylvania Dutch country shine through with chicken potpie, pork and sauerkraut, and a Dutch hash and liverwurst sandwich.

This family-owned restaurant opened optimistically in 1936, the year after the demise of the railroad from Washington. Since then it has remained synonymous with superb seafood. Now part of the Chesapeake Beach Resort & Spa, its bay-side location still provides stunning views. The extensive menu includes succulent southern Maryland specialties such as rockfish stuffed with crab imperial, fried oysters, and the region's ubiquitous crab cakes.