49 West - 49 West St Annapolis, MD 21401 (410) 626-9796
Unique Coffeehouse, Winebar & Gallery with lite fare and live music.

Acme Bar and Grill - 163 Main Street, Annapolis, MD 21401 (410) 280-6486
Downtown bar that features live music for the younger crowd.

Armadillo's Bar & Grill - 132 Dock St., Annapolis, MD 21401 (410) 280-0028
Tex-Mex themed lower level and live music upstairs on most nights.

CastleBay Irish Pub, 193 Main St., Annapolis, MD 21401 - (410) 626-0165
Downtown Irish Pub with live music on weekend nights and sometimes during the week.

Heroes Pub, 3 Riverview Avenue, Annapolis, MD 21401 - (410) 573-1996
48 beers on draft and accoustic live music.

Middleton Tavern, 2 Market Space, Annapolis, MD 21401 - (410) 263-3323
Historic taven with live music and a piano bar.

Mike's Crabhouse, 3030 Riva Road, Riva, MD 21401 - (410) 956-2784
Laid-back casual bar with outside waterfront seating. Live music and kareoke on weekends.

O'Briens Oyster Bar, 113 Main Street, Annapolis, MD 21401 - (410) 268-6288
Night club with live music and dance music. Caters to a younger crowd.

Rockfish, 400 Sixth Street, Annapolis, MD 21403 - (410) 267-1800
Upscale restaurant and large bar with live music caters to a mature audience.

Sly Fox Pub, 7 Church Circle, Annapolis, MD 21401 - (443) 482-9000
Small cozy pub and large outside area has mostly accoustic musicians. Located in the lower level of Reynolds Tavern.

Ram's Head Tavern, 33 West Street, Annapolis, MD 21401 - (410) 268-4545
Annapolis Microbrewery with local and national acts.

T.K. Sharkey's Rock'n Sports Grille, 2072 Somerville Rd, Annapolis, MD 21401 - (410) 841-5599
Very large sports bar with many large screens and games and large live music venue.

Stan & Joes Saloon, 37 West Street, Annapolis, MD 21401 - (410) 263-1993
Fun old-timey pub with an extensive menu, live music, and outdoor seating. Often very crowded.

Sly Fox Pub, 7 Church Circle, Annapolis, MD 21401 - (410) 482-9000
Live accoustic music, and outdoor seating.