Annapolis Live Music Events

Matisyahu Unplugged: 2nd Show Added by Popular Demand!

Rams Head On Stage 4 Mar 2026

2026 Annapolis St. Patrick's Hooley!

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

John Moreland & Patterson Hood

Rams Head On Stage 14 Mar 2026

Al Di Meola

Rams Head On Stage 9 May 2026

Colin James, Matt Andersen, Terra Lightfoot in Annapolis

Rams Head On Stage 6 May 2026

John Moreland and Patterson Hood

Rams Head On Stage - Annapolis 15 Mar 2026

Pete Yorn at Rams Head On Stage

Rams Head On Stage 3 Jun 2026

Stewart Copeland

Rams Head On Stage 20 Jul 2026

Ottmar Liebert and Luna Negra at Rams Head On Stage

Rams Head On Stage 4 May 2026

Al Di Meola Electric Band

Rams Head On Stage 8 May 2026

Paul Gilbert with Greg Koch

Rams Head On Stage - Annapolis 13 May 2026

Friends for Friends

Fluegel Alumni Center 14 May 2026

Candlelight: Tribute to Queen & The Beatles

Maryland Hall For The Creative Arts 3 Apr 2026

Pam Tillis in Annapolis

Rams Head On Stage 12 Apr 2026

Uli Jon Roth

Rams Head On Stage 27 Apr 2026

Marcus Miller (8:00 PM)

Rams Head On Stage 24 May 2026

Alan Doyle, Bandits on the Run in Annapolis

Rams Head On Stage 30 Apr 2026

Madeleine Peyroux

Rams Head On Stage 10 May 2026

The Yardbirds in Annapolis

Rams Head On Stage 2 Mar 2026

Tommy Castro & The Painkillers

Rams Head On Stage - Annapolis 20 Apr 2026

Annapolis First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 3 May 2026

Candlelight: 90s Unplugged

Maryland Hall 18 Jul 2026

Eddie Money Legacy Band at Rams Head On Stage

Rams Head On Stage 17 Apr 2026

Albert Castiglia

Rams Head On Stage - Annapolis 7 Mar 2026

Live and Let Die: The Music of Paul McCartney

Rams Head On Stage 10 May 2026

Pam Tillis

Rams Head On Stage 16 Aug 2026

Alan Doyle

Rams Head On Stage 29 Apr 2026

Duane Betts at Rams Head On Stage

Rams Head On Stage 21 Apr 2026

Ally Venable

Rams Head On Stage 20 Apr 2026

Eastport Oyster Boys 30th Anniversary Shuck It Tour Celebration

Maryland Hall 22 Mar 2026

End of the Line - Allman Brothers Tribute

Rams Head On Stage - Annapolis 21 Mar 2026

David Wax Museum

Rams Head On Stage - Annapolis 11 Apr 2026

Sirens of Spring Tour feat. Mama’s Black Sheep, Sweet Leda Duo, Regina Sayles & Colleen Clark

Rams Head On Stage 7 May 2026

Thursday Night LIVE! Featuring The Chucks

307 Sail Pl, Annapolis, MD 21401, United States 11 Jun 2026

Thursday Night LIVE! Featuring Sweet Leda

307 Sail Pl, Annapolis, MD 21401, United States 4 Jun 2026

The High Kings (8:00pm)

Rams Head On Stage 8 Mar 2026

The Reverend Peyton's Big Damn Band

Rams Head On Stage - Annapolis 30 Apr 2026

Thursday Night LIVE! Featuring Dan Heely

307 Sail Pl, Annapolis, MD 21401, United States 30 Jul 2026

Thursday Night LIVE! Featuring 8 Ohms

307 Sail Pl, Annapolis, MD 21401, United States 6 Aug 2026

Nao Yoshioka

Rams Head On Stage 27 May 2026

The UN-Gala GALA

Great Frogs Winery 18 Apr 2026

An Evening with Chris Trapper

49 West Coffeehouse, Winebar & Gallery 25 Apr 2026

Jeff Coffin

Rams Head On Stage 13 Apr 2026

Parking Los Straitjackets

Rams Head On Stage - Annapolis 15 Mar 2026

LIVE MUSIC: Suzy & Shawn in downbar

Rams Head Tavern Annapolis 28 Feb 2026

Bobby Thompson and Karen Jonas in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 16 Mar 2026

Jazz at Lincoln Center PRESENTS: Great American Crooners

801 Chase St, Annapolis, MD, United States, Maryland 21401 13 Apr 2026

An Evening with Branford Marsalis

801 Chase St, Annapolis, MD, United States, Maryland 21401 1 Mar 2026

Green River: 15th Anniversary Legacy Tour

Rams Head On Stage 7 Mar 2026

The Samples with Kieran Lally

Rams Head On Stage - Annapolis 30 May 2026

Special Guest’s Debut at Ram’s Head Tavern Downbar March 20th

Rams Head Tavern Annapolis 20 Mar 2026

Nao Yoshioka at Rams Head On Stage

Rams Head On Stage 28 May 2026

Music Trivia - Cape Vibes Fundraiser!!

Cape St. Claire Improvement Association 27 Feb 2026

The Aggrolites

Rams Head On Stage 11 Mar 2026

Ridge Grow Grand Opening

244 S Old Mill Bottom Rd, Arnold, MD 4 Apr 2026

Cole Chaney & The Local Honeys

Rams Head On Stage 6 Apr 2026

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis 26 Mar 2026

LIVE MUSIC with ONO Band

Blackwall Hitch - Annapolis 28 Feb 2026

Dogfather's Blues Jam

Dark Horse Annapolis 15 Mar 2026

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis 2 Apr 2026

PMA Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 7 Jun 2026

Jackrabbit at Rams Head On Stage

Rams Head On Stage 30 May 2026

The Reverend Peyton's Big Damn Band

Rams Head On Stage 29 Apr 2026

Femmes of Rock

Rams Head On Stage 24 Apr 2026

ALO DOES ELO AT ANNAPOLIS SMOKEHOUSE!

Annapolis Smokehouse and Tavern 23 May 2026

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 27 Feb 2026

Pierce Pettis with Special Guest Danielle Howle in Annapolis

49 West Coffeehouse, Winebar & Gallery 17 Aug 2026

Parking Spyro Gyra

Rams Head On Stage - Annapolis 6 Mar 2026

Jeffrey Gaines, Sawyer Fredericks in Annapolis

Rams Head On Stage 1 Mar 2026

John Moreland at Rams Head On Stage

Rams Head On Stage 15 Mar 2026

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 21 May 2026

Mike Doughty at Rams Head On Stage

Rams Head On Stage 11 Apr 2026

Karyn Oliver and Miles & Mafale in Annapolis

49 West Coffeehouse, Winebar & Gallery 20 Jul 2026

Rams Head Roadhouse

Ramshead Roadhouse 7 Mar 2026

Rams Head Roadhouse

Ramshead Roadhouse 6 Jun 2026

Ramshead Tavern downtown Annapolis

Rams Head Tavern Annapolis 12 Mar 2026

Resonance & Renewal: A Spring Sound Bath for Self-Compassion

333 Dubois Rd 18 Apr 2026

Michael K. at Rams Head Roadhouse

Rams Head Roadhouse 27 Feb 2026

Justin Taylor | Annapolis MD

307 Sail Pl Annapolis MD 21401 13 Aug 2026

Yachtley Crew

Maryland Hall 28 Jul 2026

Rumours ATL: A Fleetwood Mac Tribute

Rams Head On Stage 25 Jun 2026

Colin James at Rams Head On Stage

Rams Head On Stage 6 May 2026

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

Annapolis 30 Oct 2025

Parking End of the Line - Allman Brothers Tribute

Rams Head On Stage - Annapolis 21 Mar 2026

Duane Betts & Palmetto Motel

Rams Head On Stage 20 Apr 2026

Colin James Matt Anderson & Terra Lightfoot

Rams Head On Stage 5 May 2026

Jesse & Dez Money - The Eddie Money Band

Rams Head On Stage - Annapolis 18 Apr 2026