Annapolis Live Music Events

War in Annapolis

Rams Head On Stage 26 Sep 2025

War in Annapolis

Rams Head On Stage 25 Sep 2025

The Wallflowers, Brother Elsey in Annapolis

Rams Head On Stage 23 Sep 2025

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

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

Annapolis, MD 20 Sep 2025

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

10,000 Maniacs

Rams Head On Stage 13 Sep 2025

10000 Maniacs at Rams Head On Stage

Rams Head On Stage 13 Sep 2025

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

Calvert Street Stage 12 Sep 2025

Chris Standring in Annapolis

Rams Head On Stage 10 Sep 2025

Maysa (8:30 PM)

Rams Head On Stage 20 Sep 2025

Keb' Mo' in Annapolis

Maryland Hall 21 Nov 2025

Chris Standring in Annapolis

Rams Head On Stage 10 Sep 2025

10,000 Maniacs

Rams Head On Stage 14 Sep 2025

Hermans Hermits

Rams Head On Stage 27 Sep 2025

Skerryvore in Annapolis

Rams Head On Stage 8 Sep 2025

Casey Abrams

Rams Head On Stage 14 Sep 2025

The Robert Cray Band in Annapolis

Rams Head On Stage 22 Sep 2025

West Annapolis Oktoberfest 2025

Annapolis Street, Annapolis, MD, United States, Maryland 21401 28 Sep 2025

Richard Thompson in Annapolis

St. John's College - Francis Scott Key Auditorium 2 Nov 2025

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

Rams Head On Stage 26 Sep 2025

Casey Abrams in Annapolis

Rams Head On Stage 15 Sep 2025

Robert Cray in Annapolis

Rams Head On Stage 22 Sep 2025

Shaun Cassidy at Rams Head On Stage

Rams Head On Stage 18 Oct 2025

Crack the Sky

Rams Head On Stage 1 Nov 2025

Najee in Annapolis

Rams Head On Stage 9 Nov 2025

The Australian Bee Gees

Rams Head On Stage 4 Oct 2025

Sheena Easton in Annapolis

Rams Head On Stage 9 Sep 2025

Close Enemies

Rams Head On Stage 11 Oct 2025

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

Rams Head On Stage 3 Oct 2025

Lily Grace Live @ Annapolis Songwriters Festival 2025

33 West St, Annapolis, MD 21401-2574, United States 12 Sep 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

American Aquarium in Annapolis

Rams Head On Stage 8 Oct 2025

Party in the Port

317 First St, Annapolis, MD, United States, Maryland 21403 11 Oct 2025

Acoustic Alchemy

Rams Head On Stage 12 Nov 2025

Michael McHenry Tribe-Saturday inside at Middleton Tavern - TONIGHT

Middleton Tavern 6 Sep 2025

Dirty Heads

Calvert Street Stage 11 Sep 2025

Steep Canyon Rangers at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 11 Sep 2025

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

Rams Head On Stage 24 Oct 2025

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

33 West St, Annapolis, MD, United States, Maryland 21401 5 Oct 2025

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

Rams Head On Stage 24 Oct 2025

The Amish Outlaws return to Rams Head On Stage

Rams Head On Stage 17 Oct 2025

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

Maryland Hall 11 Sep 2025

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

Rams Head On Stage 5 Oct 2025

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

Maryland Hall 23 Nov 2025

Chris Isaak in Annapolis

Maryland Hall 7 Dec 2025

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

Rams Head On Stage 9 Oct 2025

Annapolis Fall Italian Festa

620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

Boatyard Beach Bash

723 2nd St, Annapolis, MD, United States, Maryland 21403 20 Sep 2025

Rose Terrace at Reynolds Tavern

7 Church Cir, Annapolis, MD, United States, Maryland 21401 11 Sep 2025

Argentinian Asado Party Fundraiser hosted by Coast to Coast 4 ALS

Annaplolis Maryland 13 Sep 2025

Pat McGee & Friends : All Request Show (Matinee)

Rams Head On Stage 7 Sep 2025

Marshall Crenshaw: 40+ Years in Showbiz

Rams Head On Stage 14 Nov 2025

Rooftop Thursdays with Dave Tieff

Blackwall Hitch - Annapolis 11 Sep 2025

Yasmin Williams at Rams Head On Stage

Rams Head On Stage 2 Oct 2025

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

33 West St, Annapolis, MD, United States, Maryland 21401 18 Oct 2025

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

Rams Head On Stage 28 Sep 2025

Noelle & Jeff Full Band!

Middleton Tavern 3 Oct 2025

Najee in Annapolis

Rams Head On Stage 9 Nov 2025

10 000 Maniacs

Rams Head On Stage 12 Sep 2025

Dustbowl Revival w/ Chris Kasper

Rams Head On Stage 7 Sep 2025

Joe Pug at Rams Head On Stage

Rams Head On Stage 27 Sep 2025

Siren's Call

The Westin Annapolis 19 Sep 2025

Marshall Crenshaw at Rams Head On Stage

Rams Head On Stage 14 Nov 2025

Dinner Under the Stars

West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401 10 Sep 2025

Colin Hay in Annapolis

St. John's College - Francis Scott Key Auditorium 11 Nov 2025

Siren's Call

The Westin Annapolis 26 Sep 2025

Julian Lage at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 4 Oct 2025

Siren's Call

The Westin Annapolis 12 Sep 2025

Dan Navarro w/ Jesse Lynn Madera

Rams Head On Stage 6 Nov 2025

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 7 Sep 2025

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

Rams Head On Stage 16 Sep 2025

Music of the Americas - September 21, 2025

Maryland Hall 21 Sep 2025

Rooftop Thursdays with Andrew Bell

Blackwall Hitch - Annapolis 2 Oct 2025

Will Hoge at Rams Head On Stage

Rams Head On Stage 16 Nov 2025

Siren's Call

The Westin Annapolis 3 Oct 2025

Herman's Hermits

Rams Head On Stage 27 Sep 2025

Band of a Thousand Names

Rams Head On Stage 11 Oct 2025

Annapolis Songwriters Festival with Watermark Songwriter On The Severn

1 Dock St, Annapolis, MD, United States, Maryland 21401 13 Sep 2025

Robert Cray Band at Rams Head On Stage

Rams Head On Stage 22 Sep 2025

Maysa at Rams Head On Stage

Rams Head On Stage 20 Sep 2025

Siren's Call

The Westin Annapolis 10 Oct 2025

The Martin Sexton Abbey Road Show at Rams Head On Stage

Rams Head On Stage 21 Nov 2025

Grand Finale Party

317 First Street, 21403 27 Sep 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

SOFO Summer Drive-In Movies Under the Stars - September 2025

Bay Ridge Plaza 123 Hillsmere Dr, Annapolis MD 21403 26 Sep 2025

Noelle & Jeff Full Band!

Middleton Tavern 12 Sep 2025

Pure Prairie League at Rams Head On Stage

Rams Head On Stage 5 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

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

Rams Head On Stage 26 Dec 2025

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 8 Nov 2025

Siren's Call

The Westin Annapolis 17 Oct 2025

Singer Songwriter Showcase 2025

189 Main St, Annapolis, MD, United States, Maryland 21401 13 Sep 2025

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

Rams Head On Stage 6 Oct 2025

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

Rams Head On Stage 15 Oct 2025

Chris Isaak

Maryland Hall For The Creative Arts 6 Dec 2025

Rams Head Presents Chris Isaak - Annapolis, MD

Maryland Hall 7 Dec 2025

Official Annapolis Baygrass Kickoff Party: Fitzkee Brothers & Wicked Sycamore

Maryland Hall 19 Sep 2025

Tunes Through Time: The Sounds of Early Annapolis

43 Pinkney St, Annapolis, MD 21401-1717, United States 13 Sep 2025