Whether you’re seeking an intimate speakeasy experience or a great happy hour, Annapolis has loads of choices when it comes to bars. Located on the Chesapeake Bay at the mouth of the Severn River, many of Annapolis’ bars have an innate charm and a long history that precedes the Prohibition Era. We compiled a short but diverse list of some of Annapolis’ best bars so you can enjoy some fun things to do in Annapolis at night! All of the bars below are clustered around the historic Maryland State House downtown so walking between them is easy. After a fun-filled day of downtown Annapolis activities, head to one of the bars below!
Boatyard Bar & Grill
Best known for their seafood, Boatyard Bar & Grill is a family friendly restaurant located just across the Annapolis Harbor from the Maryland State House. Sit with views of the water and dine on Boatyard’s famous crab cakes, oysters, and raw fish during their weekday Happy Hour.
For drinks, Boatyard boasts an impressive global wine list, over a dozen specialty cocktails, a large menu of neat liquors, and both bottled and draft beers. If you’re looking for a nautical themed bar with a great atmosphere, great food, and that’s also family-friendly to boot, then Boatyard should be your go-to.
Galway Bay Irish Restaurant & Pub
No trip to Annapolis should be complete without going to one of its famous Irish pubs. Galway Bay is a lively pub that features Gaelic treats and American classics served in a cozy, brick-walled building. With walls decorated in antique trinkets and booths made from reclaimed wood, Galway Bay is a great place to warm up on a rainy day or meet with friends in a relaxed and intimate atmosphere. For drinks, Galway is best known for their Irish cocktails and Guinness beer. They also have over 10 beers on draft, many bottled beers, and house wine.
Located on Main Street downtown, Dry 85 is an intimate speakeasy-style nook with 1920s flair. Dry 85 offers whiskey, beer, and refined takes on American comfort food. With dark walls and old booths for convening, Dry 85 is the perfect place to taste some of Annapolis’ best selections of whiskeys, ryes, bourbons and scotches.
Dry 85 serves over five different flights of whiskey, which include whiskeys made around the world. Impressive to say the least, their cocktail menu also checks all of the boxes for Prohibition Era classics, favorites, and contemporary house cocktails. If you’re looking for a neat glass of grain alcohol or a perfectly balanced cocktail, Dry 85 should be the first place to check out.
Enjoy Fun Things to Do in Annapolis at Night Near Our Rentals
Stay within walking distance of Annapolis’ best bars by staying in one of our beautiful vacation homes. Each one of the elegant homes we offer were hand-picked by one of our experienced property managers.
Each guest gets the opportunity to consult with a booking specialist to ensure you choose the right vacation home for your needs. We personally oversee all aspects of the rental preparations and are confident that our homes will exceed your expectations. Browse our available rentals in Annapolis such as our pet friendly vacation rentals or rentals with a pool today and enjoy the many downtown Annapolis activities!