8 Best Restaurants in Annapolis and Southern Maryland, Maryland

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.

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.

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.

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.