Annapolis Nightlife – Fun Activities in Annapolis MD

Everyone has their own idea of the perfect night out on the town. Whether you desire to go to dinner, get drinks, or see live music, Annapolis has plenty of fun for everyone to enjoy. We selected a few of our favorite nighttime activities in Annapolis to share with you. Read on to explore all of the fun activities in Annapolis, MD to do after dark!

Where to Grab Dinner

Best known for its seafood, no trip to Annapolis would be complete without tasting the famous oysters or Maryland crab. To get great seafood, head to Boatyard Bar & Grill and the Annapolis Oyster Bar. Both restaurants have a great selection of fresh seafood in a beautiful atmosphere. Annapolis Oyster Bar is located at the heart of downtown by the historic Maryland State House. Take a pedicab across the Annapolis Harbor to eat on the water at Boatyard Bar & Grill

If seafood isn’t your thing, there are still plenty of other delicious food options in Annapolis. Galway Bay Irish Restaurant & Pub is a cozy, brick-walled pub that serves Gaelic fare and American classics. With a rustic, antique vibe, Galway Bay is the perfect place to grab both dinner and drinks in an intimate atmosphere.

One of our favorite places to eat in Annapolis is Osteria 177, which serves upscale coastal Italian fare in a contemporary, white-linen restaurant. On the menu, you can expect to see well-prepared fish, an impressive selection of Italian pasta classics, and meat dishes that melt in your mouth. Head to Osteria 177 for an ultimate night of high-end dining.

Where to Grab Drinks

Downtown Annapolis is stuffed full of amazing bars that are all walking distance from one another. Clustered around the historic Maryland State House, Dry 85, Galway Bay Irish Restaurant & Pub, and Mills Fine Wine & Spirits are a few of our favorite haunts.

Located on Main Street, Dry 85 is an intimate speakeasy-style bar. Serving an impressive list of bourbon, rye, global whiskeys, beer, wine, and classic cocktails, Dry 85’s selection is unmatched. With black walls and wood floors, Dry 85 creates the perfect atmosphere for a cozy or intimate night out.

Mentioned above in our list of favorite restaurants, Galway Bay Irish Restaurant & Pub is also a great option for drinks. Boasting exposed brick walls, antique artifacts hung on the walls, and reclaimed wood booths, Galway Bay is a cozy neighborhood staple. Galway Bay serves up classic Irish cocktails, Guinness, American beer on draft, bottled beer, and house wine, making it a great kickback spot.

If you prefer to bring the nightlife to you, Mills Fine Wine & Spirits is our go-to place to get quality wine and liquor for a night in. Located in an old brick building, Mills has an impressive selection of global wines and locally distilled spirits that are sure to help make your night in unique.

Where to See Live Music

Walking through historic downtown Annapolis, you’re likely to hear the sounds of live music filling the streets nightly. Many local pubs and restaurants host live bands every day of the week, but music is also played on outside patios and on street corners in the summertime.

For an incredible evening of music, head to Rams Head on Stage, Annapolis’ most famous music venue. It draws phenomenal music from a wide range of genres like soul, rock, blues, jazz, country, reggae, funk, and everything in between. Rams Head’s intimate sit-down venue is the ultimate place to see live music in Annapolis, and a visit here is sure to be one of your favorite activities in Annapolis, MD.

Stay Near Your Favorite Activities in Annapolis MD

Stay close to the restaurant, bar, or live music in downtown Annapolis by staying in one of our beautiful vacation rentals. Each one of the elegant rentals we offer are hand-selected and furnished to offer unmatched comfort. We personally oversee all aspects of the rental preparations and we’re confident that your expectations will be exceeded in our beautiful homes. Browse our available rentals in downtown Annapolis today or pet friendly rentals and enjoy the many fun activities in Annapolis, MD!

(443) 837-6870