Main Street is the essence of Annapolis. From the top of the street, views of the Annapolis Harbor are met with historic buildings occupied by boutiques, art galleries, restaurants, gift shops. It has a little bit of everything. Main Street offers fine Italian dining, a taco bar, seafood, American fare, Irish food, sushi, French cuisine, a gastropub speakeasy, pizza shops, ice cream parlors, and coffee shops (to name just a few). It’s also the nightlife hub of Annapolis, offering live music at the many taverns, pubs and bars, making for a perfect night out in Annapolis.


West Street is another one of Annapolis’ iconic streets. Aside from a number of great eateries, it’s also known as the Annapolis Art District. Packed next to art galleries and live music venues you’ll find coffee shops, a Thai restaurant, Italian, Mexican, sushi, and bistros for starters. Pairing with these great dining spots is Dinner Under the Stars, where the first block of the street is closed to traffic and the restaurants offer an al fresco dining experience complete with live music under a canopy of lights. Happening each Wednesday night (July – September), it’s the perfect dining experience in Annapolis.