Where to Catch Live Music in Annapolis

Annapolis may be known for its sailboats, historical buildings, and waterfront views, but don’t sleep on its live music scene. Whether you’re into acoustic sets, rollicking Irish tunes, or full-on rock shows, there’s a stage (or corner) waiting for you. Here are a few of our local favorites where the music is always on key.

Rams Head On Stage
This one’s basically the crown jewel of Annapolis music venues. Rams Head On Stage brings in national touring acts, comedy shows, and local favorites in an intimate, sit-down setting. It’s the kind of place where you can sip a craft beer, hear every lyric, and maybe even brag later that you saw them before they got big.

Federal House Bar & Grille
By day, it’s a lively pub with some of the best crab dip in town. By night, on the weekends, it transforms into Club Fed, with a rotating lineup of DJs that keep the dance floor packed. If you’re in the mood for something more low-key, Federal House also hosts acoustic music nights where you can just kick back, grab a drink, and soak in the sounds. 

O’Loughlin’s Restaurant & Pub
Arnold locals know this is the spot for friendly vibes, cold drinks, and a steady lineup of live music. From cover bands to local rockers, O’Loughlin’s keeps the energy high and the nights fun. It’s your favorite neighborhood bar with a killer soundtrack.

Middleton Tavern
History meets harmony at Middleton Tavern, where the piano bar on Friday and Saturday nights is a true Annapolis treasure. There’s something magical about a packed room singing along while the pianist takes requests and keeps the party going. If you haven’t closed out a night here, you haven’t done Annapolis right.

Galway Bay
Step into Galway Bay and you’ll feel like you’ve been transported straight to Ireland. The traditional Irish music, played on Sundays, is a great way to cap off the weekend. Pair that with a pint of Guinness and maybe some shepherd’s pie, and suddenly you’ve found your new favorite tradition.

49 West Coffeehouse, Winebar & Gallery
For something more intimate, 49 West is a gem. It’s part coffeehouse, part wine bar, part art gallery, and yes, a music venue too. Their calendar is packed with jazz, folk, and singer-songwriter nights that make it feel like a creative hub right in the heart of the city.

Twain’s Tavern
Head a little north to Pasadena and you’ll find Twain’s Tavern, a high-energy spot with a full calendar of live music and special events. It’s spacious, lively, and perfect if you’re looking to dance the night away with a bigger crowd.

The Jetty
Music with a view? Yes, please. The Jetty in Grasonville (just over the Bay Bridge) is famous for its waterfront stage, where bands play as the sun sets over the water. It’s part beach party, part concert, and 100% worth the drive.

Rumor Reel
Another waterfront favorite in Pasadena, Rumor Reel mixes live music with great food and cocktails. The vibe is fun and festive, especially when the band is cranking and the dockside crowd is dancing.

Annapolis is a fun, walkable city where you can hop from one venue to another in a single night. Start with dinner and music at Federal House, wander over to Rams Head for one of their ticketed shows, and then close the night at Middleton’s piano bar. That’s what we call hitting all the right notes.