Annapolis Live Music Events

2026 Annapolis St. Patrick's Hooley!

U.S. Naval Academy Alumni Association & Foundation 7 Mar 2026

Siren's Call

The Westin Annapolis 26 Dec 2025

Scorpion Rose

Blackwall Hitch - Annapolis 20 Dec 2025

Tides & Tunes

The Westin Annapolis 16 Dec 2025

Tides & Tunes

The Westin Annapolis 23 Dec 2025

December Film Club - "The Exterminating Angel" (1962)

AND Creative Studio 19 Dec 2025

Rams Head Presents The Bacon Brothers: Freestanding Tour - Maryland Hall - Annapolis, MD

Maryland Hall 22 Jan 2026

Ana Popovic: Dance To The Rhythm Tour (Matinee)

Rams Head On Stage 11 Jan 2026

Fireside Revelry: A Colonial Twelfth Night Concert

19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 10 Jan 2026

Siren's Call

The Westin Annapolis 19 Dec 2025

Dead Letter Office: A Tribute of R.E.M

Rams Head On Stage 11 Jan 2026

LIVE MUSIC with Moon Cherry

Blackwall Hitch - Annapolis 19 Dec 2025

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 26 Dec 2025

G Love and Special Sauce at Rams Head On Stage

Rams Head On Stage 3 Feb 2026

Bill Starks with Greg Hardin in Annapolis

49 West Coffeehouse, Winebar & Gallery 20 Jan 2026

Candlelight: Christmas Carols on Strings | Annapolis

Annapolis Waterfront Hotel 21 Dec 2025

LIVE MUSIC with Enslow

Blackwall Hitch - Annapolis 26 Dec 2025

Cash Unchained – The Ultimate Johnny Cash Tribute

Rams Head On Stage 22 Jan 2026

DMTB: The Dave Matthews Tribute Band: Tomorrow We Die Tour

Rams Head On Stage 25 Jan 2026

January Film Club - "Passion of Joan of Arc" (1928) w/ live music accomp

AND Creative Studio 23 Jan 2026

Bruce in the USA: The World's #1 Tribute to Bruce Springsteen and the E Street Band

Rams Head On Stage 23 Jan 2026

SQRRL! HOLIDAY! Kids Musical Extravaganza! MATINEE SHOW w/ The Christmas Wish Crackler!

Rams Head On Stage 20 Dec 2025

LIVE MUSIC with Aiden Ewald

Blackwall Hitch - Annapolis 18 Dec 2025

Tides & Tunes

The Westin Annapolis 30 Dec 2025

Fallin' Free: A Tribute to Tom Petty & The Heartbreakers feat. Scott Kurt

Rams Head On Stage 21 Feb 2026

The Dave Matthews Tribute Band

Rams Head On Stage 24 Jan 2026

Sons of Cream feat. Kofi Baker & Malcolm Bruce w/ special guest Rob Johnson

Rams Head On Stage 27 Feb 2026

Bobby Thompson and Karen Jonas in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 16 Mar 2026

The High Kings in Annapolis

Rams Head On Stage 8 Mar 2026

Jonathan Butler in Annapolis

Rams Head On Stage 18 Apr 2026

Bay Winds Band Holiday Winter Concert "Set the Scene" with Holiday Fun!

Unity by the Bay (Maryland) 16 Dec 2025

Marcus Miller (8:00PM)

Rams Head On Stage 24 May 2026

Dio Rules: A Tribute to Rainbow, Black Sabbath & Dio

Rams Head On Stage 19 Feb 2026

🎸The Linda Ronstadt Experience w/American Idol Star Tristan McIntosh Returns to Rams Head

Rams Head Tavern Annapolis 26 Feb 2026

Matisyahu

Rams Head On Stage 4 Mar 2026

Satisfaction - The International Rolling Stones Tribute Show

Rams Head On Stage 31 Jan 2026

G. Love & Special Sauce - Lemonade 20th Anniversary Tour with Special Guest MAKUA

Rams Head On Stage 4 Feb 2026

The Billy Price Band & The Chris O'Leary Band (Matinee)

Rams Head On Stage 1 Feb 2026

Spyro Gyra in Annapolis

Rams Head On Stage 5 Mar 2026

Naptown Brass Band Mardi Gras at Rams Head!!!

Rams Head On Stage 17 Feb 2026

Hyland Brothers Live @ Stan & Joe’s

Stan and Joe's Saloon 21 Jan 2026

Red Betty and the Ruckus at Eastport Democratic Club

Eastport Democratic Club 11 Feb 2026

G. Love & Special Sauce- Lemonade 20th Anniversary Tour with Special Guest MAKUA

Rams Head On Stage 3 Feb 2026

Mike Dawes in Annapolis

Rams Head On Stage 5 Feb 2026

Madeleine Peyroux

Rams Head On Stage 10 May 2026

Uli Jon Roth

Rams Head On Stage 27 Apr 2026

Penny and Sparrow in Annapolis

Rams Head On Stage 9 Apr 2026

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

Annapolis 30 Oct 2025

Bacon Brothers at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 22 Jan 2026

Duane Betts at Rams Head On Stage

Rams Head On Stage 21 Apr 2026

Stephen Kellogg at Rams Head On Stage

Rams Head On Stage 29 Dec 2025

Madeleine Peyroux in Annapolis

Rams Head On Stage 11 May 2026

Kashmir: The Spirit of Led Zeppelin LIVE feat. Jean Violet

Rams Head On Stage - Annapolis 11 Jan 2026

Stephen Kellogg

Rams Head On Stage - Annapolis 30 Dec 2025

Quinn Sullivan at Rams Head On Stage

Rams Head On Stage 21 Mar 2026