5 Annapolis Bars You Must See - Best Bar Crawl
- nancy9487
- 7 days ago
- 3 min read
Updated: 4 days ago
As a local, I've had the opportunity to check out the best bars and nightlife in the Annapolis downtown historic district. Trust me, there are some fantastic spots, and I'm excited to share a few of my favorites with you! I love bars that have a great atmosphere, something unique, and, of course, delicious cocktails. These top 5 Annapolis Maryland bars I've highlighted below absolutely deliver and are a must see. Ideally, they're all within walking distance of each other - perfect for an amazing bar crawl on a special night out.
Galway Bay Irish Restaurant & Pub
I enjoy starting here because the food is fantastic, and it's wise to begin a bar crawl on a full stomach! The atmosphere is very authentic - you'll feel as if you're enjoying a pint in Ireland. Since 2000, Galway Bay has been recognized as one of the Best Irish Pubs and continues to hold that title. They offer a full calendar of events including live music and pub quizzes. It's a must visit and Annapolis tradition.
Unique Offering: Year-round Egg Nog Coctail Menu!
The Parley Room, opened in 2022, is a chic cocktail bar exuding a 1920s atmosphere. Located in the historic Capital Hotel, it transports you back in time with its elegant speakeasy ambiance. With a spacious outdoor patio, it's the perfect place to enjoy a drink on a pleasant afternoon or evening in Annapolis. Voted the best cocktails in Annapolis by What's Up Media in 2025, the Parley Room is a destination you shouldn't miss!
Specialty Cocktails: Ancho Cricket & Cafe Parley
History, history, history! That's why the Drummer's Lot is a must see pub. Located in The Maryland Inn (1784), the Drummer's Lot became a popular gathering spot for locals and visitors in the 18th century, with notable figures like Ben Franklin and John Adams reportedly enjoying a drink there. Today, it continues to be a favorite spot for both locals and tourists, providing a cozy and charming atmosphere that makes it a perfect stop on our unique pub crawl.
Ghost Sightings: Captain Campbell and his bride are known to haunt the pub and the inn.
Ponche Tiki Bar, located above the Pearl Restaurant in the heart of downtown Annapolis, takes tiki decor to another level. The atmosphere and delicious cocktail menu offer a full Caribbean experience—so fun! Ponche also offers excellent happy hours and karaoke nights throughout the week. Be sure to try their famous artisanal pizzas when in town.
Ambiance: Best Island Vibe & Decor
Middleton's Piano Bar offers the perfect ending to your night! Open on Fridays and Saturdays from 9:00 pm to 1:00 am, you will need to arrive early if you want a seat. The upstairs space is so charming and cozy, but also very small. Pianist David Wolcott provides outstanding entertainment and is open to all sorts of requests. Before long, everyone is singing and dancing together—highly recommend you stop by!
History: This historic tavern is one of the oldest continuously operating taverns in the US dating back to 1750.
I hope you have a great time on this highly entertaining self-guided Annapolis pub crawl. These are "must go places" when visiting! Below, you'll find a detailed map for this walking tour.
Check out these Top 8 Things to Do in Annapolis also!