16 Best Restaurants in Annapolis and Southern Maryland, Maryland

Jimmy Cantler, a native Marylander who worked as a waterman on Chesapeake Bay, founded this local institution 40 years ago. The no-nonsense interior has nautical items laminated beneath tabletops, and steamed mussels, clams, and shrimp as well as a tomato-based Maryland crab soup, seafood sandwiches, crab cakes, and much more. Water-view outdoor dining is available seasonally, and boat owners can tie up at the dock; there's limited free parking during the busy summer season so be prepared to wait.

Step inside this Irish pub, and you'll be welcomed like a member of the family. As would be expected, the corned beef and cabbage and other traditional Irish menu items (along with classic Annapolis bar food like crab and oysters) are fantastic. The bread pudding served with vanilla custard is a great way to end your meal. On Sunday, brunch is served from 10 to 1:30—the homemade corned-beef hash is simply divine—and live Irish music is performed 4–8.

There's often a line of hungry diners waiting for a table at this comfort-food haven located on the city dock, where the portions are generous, and the service is first-rate. You can enjoy breakfast all day—Benedicts and omelets are top sellers, as are the chicken and waffles and the shrimp and grits. If you've saved room for dessert, try the homemade peanut butter cup or the "shortcake" made with a Belgian waffle and topped with ice cream, strawberries, and whipped cream.

This might be the only local Italian restaurant that doesn't offer pizza or spaghetti. Instead, Osteria serves seafood from all over the world, meat, and pasta made on the premises. Northern Italian owner and chef Arturo Ottaviano offers authentic regional cuisine like grilled branzino filleted table-side and beef tenderloin with a cognac-and-green-peppercorn sauce.

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.

You can walk, catch a water taxi from City Dock, or drive over the Spa Creek drawbridge to this local favorite in Eastport. Whether you dine indoors or out, the view of historic Annapolis and its harbor is spectacular. Any of the entrées, including the herb-encrusted rockfish or grilled filet mignon, can be turned into a four-course meal with the addition of soup, salad, and dessert.

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.

In the shadow of the state house, this understated establishment has long held a reputation for quality food and attentive service that ensures bustle year-round, especially during the busy days of the legislative session (early January into early April) and special weekend events at the Naval Academy. The menu clearly reflects the city's maritime culture, but also has seasonal specialties. The sidewalk café is open, weather permitting, April through October.

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 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.

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.

Popular with boaters who tie right up to the dock, this restaurant overlooking Island Creek has one dining room that actually juts out over the water and another on higher ground with great views from its floor-to-ceiling windows. There's also ample seating—and a tiki bar—outside. Stoney's hefty crab cakes are made with plenty of back-fin meat and little filler. Oyster sandwiches and Stoney's Steamer—handpicked selections of fresh seafood—are also good choices. The intense, house-made desserts, such as the strawberry shortcake and Kim's key lime pie, are not for the faint of heart. If you miss Stoney's in Broomes Island, there are two other locations in Solomons Island.