Iron Rooster is one of the most popular restaurants in town, known for breakfast ALL day as well as their delicious RoosTarts. Iron Rooster opened their doors 6 years ago in the heart of the colonial district of Annapolis. Surrounded by the history of Annapolis' historic cobblestone streets and candy colored row homes, they've made history of their own with their breakfast-all-day concept, tantalizing RoosTarts and boozy bloody marys!

Located in Park Place, Miss Shirley’s is a fan favorite on Food Network’s Diners, Drive-Ins and Dives and has received numerous accolades from local and national publications. Their southern inspired brunch menu is delicious and they are always experimenting with new dishes and flavor combinations to keep diners coming back for more!

The Boatyard’s “all killer, no filler” crab cakes are famous all the way to the White House and beyond. Named "Best Crab Cakes" by Baltimore Magazine. Located in the charming historic maritime neighborhood of Eastport, the Boatyard Bar & Grill is just a short walk from downtown or a quick trip on the water taxi whether for breakfast, lunch or dinner.

Right on the water in the heart of downtown Annapolis, The Choptank has many selections that are freshly caught in Maryland’s Chesapeake Bay. Enjoy their famous steamed blue crabs and crab cakes that are seasoned with The Choptank’s own special proprietary recipe. The menu also includes oysters, soups, sandwiches, entrees and house-battered Eastern Shore fried chicken.

Awarded the “Best in Dockside Dining”, Pusser’s offers fresh Chesapeake seafood, tasty Caribbean fare and a colorful selection of tropical drinks, including the world famous Pusser’s Painkiller. You have to try Emily's favorite drink, the Orange Crush; a nearly thirty-year-old recipe that originated from Ocean City, Maryland.

Long-standing (since 1975) tavern offering dozens of craft beers plus a raw bar & pub-fare menu.

McGarvey's Saloon and Oyster Bar was conceived by Air Force Captain Michael Ashford (Retired) in the summer of 1974. In fact, the name "McGarvey" itself comes from his grandmother's maiden name. Capt. Ashford instituted many of the reasons we love McGarvey's so much from: the turn-of the century décor, to their fresh selection on the raw bar menu, and the large ficus growing out of the floor of the Oyster Bar.

Established in 1830, located on Market Space in the Historical District of Annapolis, The Federal House is nestled among a shopping and sightseeing haven.

Enjoy live music during the week, DJ Cuban on Friday, and DJ Dev on Saturday nights.

Established in 1750 by owner Samuel Horatio Middleton, Middleton Tavern is one of the oldest continually operating taverns in the United States. George Washington, Thomas Jefferson, and Benjamin Franklin are among its prominent patrons. The tavern was frequented by members of the Continental Congress in 1783 and 1784.

Enjoy traditional Maryland fare in an 18th century setting on historic City Dock. Sidewalk café, raw bar, fireside dining, world famous Oyster Shooter, piano bar, and live entertainment nightly.

Fox’s Den has a cozy atmosphere that offers a great selection of American Craft Beer and Spirits along with incredible comfort food anchored by our wood-fired brick oven pizzas.

Family owned ice cream store serving downtown Annapolis since 1976.

Traditional store selling chocolates, confections & fudge, as well as original recipe ice cream.