Live Music in Annapolis

Check out happening live music events all around Annapolis, MD

War in Annapolis

 Fri, 26 Sep at 08:00 pm Rams Head On Stage

War in Annapolis

 Thu, 25 Sep at 08:00 pm Rams Head On Stage

The Wallflowers, Brother Elsey in Annapolis

 Tue, 23 Sep at 08:00 pm Rams Head On Stage

Pure Prairie League in Annapolis

 Fri, 05 Dec at 08:00 pm Rams Head On Stage

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 06:30 pm Rams Head On Stage

NILS, Jeff Kashiwa, Nils in Annapolis

 Sat, 06 Sep at 08:00 pm Rams Head On Stage

3hr Sunset Cruise w/ Live Entertainment from: KEVIN LEE

 Sat, 20 Sep at 06:00 pm Annapolis, MD

Pure Prairie League in Annapolis

 Fri, 05 Dec at 08:00 pm Rams Head On Stage

10,000 Maniacs

 Sat, 13 Sep at 08:30 pm Rams Head On Stage

10000 Maniacs at Rams Head On Stage

 Sat, 13 Sep Rams Head On Stage

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

 Fri, 12 Sep at 06:00 pm Calvert Street Stage

Chris Standring in Annapolis

 Wed, 10 Sep at 08:00 pm Rams Head On Stage

Maysa (8:30 PM)

 Sat, 20 Sep at 08:30 pm Rams Head On Stage

Keb' Mo' in Annapolis

 Fri, 21 Nov at 08:00 pm Maryland Hall

Chris Standring in Annapolis

 Wed, 10 Sep at 08:00 pm Rams Head On Stage

10,000 Maniacs

 Sun, 14 Sep at 07:30 pm Rams Head On Stage

Hermans Hermits

 Sat, 27 Sep Rams Head On Stage

Skerryvore in Annapolis

 Mon, 08 Sep at 08:00 pm Rams Head On Stage

NILS w/ Jeff Kashiwa

 Sat, 06 Sep at 08:00 pm Rams Head On Stage

Casey Abrams

 Sun, 14 Sep at 07:00 pm Rams Head On Stage

The Robert Cray Band in Annapolis

 Mon, 22 Sep at 08:00 pm Rams Head On Stage

Richard Thompson in Annapolis

 Sun, 02 Nov at 07:30 pm St. John's College - Francis Scott Key Auditorium

WAR: 50th Anniversary Tour of Why Can't We Be Friends?

Fri, 26 Sep at 08:00 pm Rams Head On Stage

Casey Abrams in Annapolis

 Mon, 15 Sep at 08:00 pm Rams Head On Stage

Robert Cray in Annapolis

 Mon, 22 Sep at 08:00 pm Rams Head On Stage

Shaun Cassidy at Rams Head On Stage

 Sat, 18 Oct at 08:00 pm Rams Head On Stage

Crack the Sky

 Sat, 01 Nov at 08:00 pm Rams Head On Stage

Najee in Annapolis

 Sun, 09 Nov at 07:30 pm Rams Head On Stage

The Australian Bee Gees

 Sat, 04 Oct at 07:00 pm Rams Head On Stage

Sheena Easton in Annapolis

 Tue, 09 Sep at 08:00 pm Rams Head On Stage

Close Enemies

 Sat, 11 Oct at 08:00 pm Rams Head On Stage

Greg Hawkes w/ Eddie Japan Performing the Music of The Cars

 Fri, 03 Oct at 08:00 pm Rams Head On Stage

Lily Grace Live @ Annapolis Songwriters Festival 2025

 Fri, 12 Sep at 07:00 pm 33 West St, Annapolis, MD 21401-2574, United States

Atlanta Rhythm Section in Annapolis

 Sat, 06 Dec at 08:00 pm Rams Head On Stage

American Aquarium in Annapolis

 Wed, 08 Oct at 08:00 pm Rams Head On Stage

Party in the Port

 Sat, 11 Oct at 06:00 pm 317 First St, Annapolis, MD, United States, Maryland 21403

Acoustic Alchemy

 Wed, 12 Nov at 08:00 pm Rams Head On Stage

Dirty Heads

 Thu, 11 Sep at 07:00 pm Calvert Street Stage

Steep Canyon Rangers at Maryland Hall for the Creative Arts

 Thu, 11 Sep at 08:00 pm Maryland Hall for the Creative Arts

Thomas Dolby: "The Iconic 80's" w/ Very Special Guest Gail Ann Dorsey

 Fri, 24 Oct at 08:00 pm Rams Head On Stage

THE AUSTRALIAN BEE GEES SHOW: A TRIBUTE TO THE BEE GEES (2ND SHOW ADDED BY POPULAR DEMAND 5:00PM)

 Sun, 05 Oct at 05:00 pm 33 West St, Annapolis, MD, United States, Maryland 21401

Thomas Dolby - The Iconic 80s at Rams Head On Stage

 Fri, 24 Oct at 08:00 pm Rams Head On Stage

Tango Reo Quintet at Annapolis City Dock Tango

 Sat, 06 Sep at 08:00 pm Annapolis City Dock

The Amish Outlaws return to Rams Head On Stage

 Fri, 17 Oct at 08:00 pm Rams Head On Stage

Rams Head Presents Steep Canyon Rangers - Maryland Hall - Annapolis, MD

 Thu, 11 Sep at 08:00 pm Maryland Hall

The Australian Bee Gees Show: A Tribute to The Bee Gees (8:00PM)

 Sun, 05 Oct at 08:00 pm Rams Head On Stage

The Ocean Blue w/ Brian Tighe of The Hang Ups (2nd Night Added!)

Thu, 09 Oct at 08:00 pm Rams Head On Stage

Annapolis Fall Italian Festa

 Sun, 21 Sep at 10:00 am 620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401

Rams Head Presents Natalie Merchant w/ Erik Della Penna: Autumn Acoustic Tour - Maryland Hall

 Sun, 23 Nov at 07:30 pm Maryland Hall

Boatyard Beach Bash

 Sat, 20 Sep at 04:00 pm 723 2nd St, Annapolis, MD, United States, Maryland 21403

Last Annapolis City Dock Tango Septemeber 2025

 Sat, 06 Sep at 07:00 pm Susan Campbell Park

Pat McGee & Friends : All Request Show (Matinee)

Sun, 07 Sep at 01:00 pm Rams Head On Stage

Marshall Crenshaw: 40+ Years in Showbiz

 Fri, 14 Nov at 08:00 pm Rams Head On Stage

Chris Isaak in Annapolis

 Sun, 07 Dec at 08:00 pm Maryland Hall

Rooftop Thursdays with Dave Tieff

 Thu, 11 Sep at 06:00 pm Blackwall Hitch - Annapolis

Yasmin Williams at Rams Head On Stage

 Thu, 02 Oct at 08:00 pm Rams Head On Stage

Shaun Cassidy: The Road To Us Tour (Annapolis, MD)

 Sat, 18 Oct at 08:00 pm 33 West St, Annapolis, MD, United States, Maryland 21401

Herman's Hermits Starring Peter Noone (7:30PM)

 Sun, 28 Sep at 07:30 pm Rams Head On Stage

Noelle & Jeff Full Band!

 Fri, 03 Oct at 10:00 pm Middleton Tavern

Dustbowl Revival w/ Chris Kasper

 Sun, 07 Sep at 08:00 pm Rams Head On Stage

West Annapolis Oktoberfest 2025

 Sun, 28 Sep at 11:00 am Annapolis Street, Annapolis, MD, United States, Maryland 21401

Joe Pug at Rams Head On Stage

 Sat, 27 Sep at 08:00 pm Rams Head On Stage

10 000 Maniacs

 Fri, 12 Sep Rams Head On Stage

Siren's Call

 Fri, 19 Sep at 05:00 pm The Westin Annapolis Free

Marshall Crenshaw at Rams Head On Stage

 Fri, 14 Nov at 08:00 pm Rams Head On Stage

Najee in Annapolis

 Sun, 09 Nov at 04:30 pm Rams Head On Stage

Dinner Under the Stars

Wed, 10 Sep at 05:00 pm West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401

Colin Hay in Annapolis

 Tue, 11 Nov at 08:00 pm St. John's College - Francis Scott Key Auditorium

Siren's Call

 Fri, 26 Sep at 05:00 pm The Westin Annapolis Free

Julian Lage at Maryland Hall for the Creative Arts

 Sat, 04 Oct at 07:30 pm Maryland Hall for the Creative Arts

Siren's Call

 Fri, 12 Sep at 05:00 pm The Westin Annapolis Free

Dan Navarro w/ Jesse Lynn Madera

 Thu, 06 Nov at 08:00 pm Rams Head On Stage

First Sunday Arts Festival

Sun, 07 Sep at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Michael Schenker: "My Years With UFO" w/ Jared James Nichols

 Tue, 16 Sep at 08:00 pm Rams Head On Stage

Music of the Americas - September 21, 2025

 Sun, 21 Sep at 03:00 pm Maryland Hall USD 0 to 28

Rooftop Thursdays with Andrew Bell

 Thu, 02 Oct at 06:00 pm Blackwall Hitch - Annapolis

Siren's Call

 Fri, 03 Oct at 05:00 pm The Westin Annapolis Free

Herman's Hermits

 Sat, 27 Sep at 07:00 pm Rams Head On Stage

Band of a Thousand Names

 Sat, 11 Oct at 08:00 pm Rams Head On Stage

Annapolis Songwriters Festival with Watermark Songwriter On The Severn

 Sat, 13 Sep at 07:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Robert Cray Band at Rams Head On Stage

 Mon, 22 Sep at 08:00 pm Rams Head On Stage

Maysa at Rams Head On Stage

 Sat, 20 Sep at 05:30 pm Rams Head On Stage

Siren's Call

 Fri, 10 Oct at 05:00 pm The Westin Annapolis Free

The Martin Sexton Abbey Road Show at Rams Head On Stage

 Fri, 21 Nov at 08:00 pm Rams Head On Stage

Will Hoge at Rams Head On Stage

 Sun, 16 Nov at 08:00 pm Rams Head On Stage

Grand Finale Party

 Sat, 27 Sep at 05:00 pm 317 First Street, 21403

Jon McLaughlin and Friends: Home For The Holidays

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Noelle & Jeff Full Band!

 Fri, 12 Sep at 10:00 pm Middleton Tavern

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 09:30 pm Rams Head On Stage

Jimmie's Chicken Shack HOLIDAZE show at Rams Head On Stage

 Fri, 26 Dec at 07:00 pm Rams Head On Stage

Siren's Call

 Fri, 17 Oct at 05:00 pm The Westin Annapolis Free

Singer Songwriter Showcase 2025

 Sat, 13 Sep at 09:00 pm 189 Main St, Annapolis, MD, United States, Maryland 21401

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

 Mon, 06 Oct at 07:00 pm Rams Head On Stage

Katie Pruitt: Time Wasn't Wasted Tour w/ Jess Nolan

 Wed, 15 Oct at 08:00 pm Rams Head On Stage

Annapolis Vintage Market-October 5th

 Sun, 05 Oct at 11:00 am 40 Hudson Street Unit 107, Annapolis, MD

Chris Isaak

 Sat, 06 Dec at 07:00 pm Maryland Hall For The Creative Arts

Rams Head Presents Chris Isaak - Annapolis, MD

 Sun, 07 Dec at 08:00 pm Maryland Hall

Official Annapolis Baygrass Kickoff Party: Fitzkee Brothers & Wicked Sycamore

 Fri, 19 Sep at 08:00 pm Maryland Hall

Signature Series: Darkness to Light

 Sat, 08 Nov at 07:30 pm Maryland Hall for the Creative Arts

Dan Navarro at Rams Head On Stage

 Thu, 06 Nov at 08:00 pm Rams Head On Stage