Pit Boys

Full service restaurant and bar

Mason's Famous Lobster Rolls brings the authentic taste of New England to Annapolis! Try our mouthwatering lobster rolls made with fresh Maine lobster. Our signature offerings are the Classic and the Connecticut Rolls. The Classic features chilled lobster served in a buttery toasted roll, with mayo, lemon-butter, and our special seasoning. For those who prefer a warm option, our Connecticut offers lobster tossed in butter, served on a warm, buttery toasted roll. For the ultimate indulgence, try either roll Bar Harbor style with 50% more lobster meat and a whole lobster tail on top. You can also try some of our other delicious offerings, including lobster mac-and-cheese, lobster grilled cheese, and N.E. Clam Chowder and Lobster Bisque,

Experience the taste of Chesapeake Bay at O'Brien's Oyster Bar & Seafood Tavern. We are a family-friendly establishment dedicated to serving the freshest seafood in Annapolis. Our menu features a variety of locally sourced seafood, from succulent oysters to classic crab cakes, all crafted to perfection. Discover a taste of history in every bite at our historic downtown location, just steps away from the waterfront. Join us for a unique dining experience where good food and rich history meet.

Opened on “Ego Alley” along downtown Annapolis’ famous City Dock, The Choptank is a classic fish & crab house serving Maryland’s famous cuisine, highlighted by steamed hard-shell blue crabs. Enjoy a cocktail, crush or one of 20 draft beer selections while listening to live local musicians on our indoor stage. The Choptank’s spacious waterfront deck and rooftop features plenty of seating so you can watch the bustling neighborhood and docks that surround you.

from our website

Longtime fixture offering classic American fare including seafood & steak plus a porch & live music.

Little Italy Annapolis is located on Forest Drive Annapolis, Maryland right next to Bruster's Ice Cream. Little Italy Annapolis is a family owned and friendly, fast casual restaurant, providing some of the tastiest Italian food in the Annapolis area, and is available for dine-in, carry-out, catering, and we offer delivery through DoorDash (some restrictions apply to the delivery). We have carefully selected menu offering traditional Italian cuisine, pizza, subs, calzones, stromboli, salads, and pasta dishes. Finish off your well-prepared meal with one of our delicious desserts, such as the traditional “pick me up” Italian dessert tiramisu. We hope to serve you soon. Ciao.

1407 Forest Dr