Annapolis Live Music Events

2026 Maryland Seafood Festival

Sandy Point State Park East Beach 12 Sep 2026

Stewart Copeland

Rams Head On Stage 20 Jul 2026

Lalah Hathaway at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 16 Nov 2026

Candlelight: 90s Unplugged

Maryland Hall 18 Jul 2026

PJ Morton

Rams Head On Stage - Annapolis 4 Aug 2026

Candlelight: A Haunted Evening of Halloween Classics

Maryland Hall 29 Oct 2026

Candlelight: Coldplay & Imagine Dragons

Maryland Hall 18 Jul 2026

Los Lonely Boys

Rams Head On Stage 29 Sep 2026

Gaelic Storm in Annapolis

Rams Head On Stage 4 Nov 2026

Los Lonely Boys at Rams Head On Stage

Rams Head On Stage 29 Sep 2026

Shawn Mullins at Rams Head On Stage

Rams Head On Stage 15 Jul 2026

Tab Benoit w/ Sgt. Splendor

Rams Head On Stage 14 Jul 2026

Ari Hest at 49 West in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 16 Nov 2026

Steve Oliver & The Grainger Brothers

Rams Head On Stage 26 Jul 2026

Pam Tillis

Rams Head On Stage 16 Aug 2026

Jimmy Charles w. Melissa Quinn Fox

Rams Head On Stage 15 Aug 2026

Digable Planets in Annapolis

Maryland Hall 5 Aug 2026

Josiah and the Bonnevilles in Annapolis

Rams Head On Stage 13 Sep 2026

The Peake Run- Our Big Ducking Run to Celebrate the 60 Years of the Maryland Seafood Festival

Sandy Point State Park 13 Sep 2026

Southern Culture On the Skids at Rams Head On Stage

Rams Head On Stage 26 Sep 2026

North Mississippi Allstars

Rams Head On Stage - Annapolis 8 Oct 2026

Who's Bad: The World's #1 Michael Jackson Tribute

Rams Head On Stage 19 Jul 2026

Annapolis First Sunday Arts Festival

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

Freddy Jones Band w. Chris Stake

Rams Head On Stage 25 Jul 2026

Steve Oliver in Annapolis

Rams Head On Stage 26 Jul 2026

Marion Meadows at Rams Head On Stage

Rams Head On Stage 24 Jul 2026

Michael Cleveland in Annapolis

Annapolis Baygrass Music Festival 20 Sep 2026

The Record Company at Rams Head On Stage

Rams Head On Stage 17 Aug 2026

Candlelight: 90s Unplugged | Annapolis

Maryland Hall 29 Oct 2026

Tango Under the Stars - City Dock Tango with Emanuel Trifilio's orchestra

West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401 15 Aug 2026

Candlelight: 90s Unplugged

Maryland Hall For The Creative Arts 17 Jul 2026

Marion Meadows & Alex Bugnon

Rams Head On Stage 23 Jul 2026

The Record Company

Rams Head On Stage 16 Aug 2026

Donavon Frankenreiter: Ask Me Anything Tour w/ Iris And The Shade

Rams Head On Stage 20 Aug 2026

Thursday Night LIVE! Featuring Honest Lee Soul

307 Sail Pl, Annapolis, MD 21401, United States 16 Jul 2026

Peter Levin (Gregg Allman’s Keyboard Player) with The Fitzkee Brothers

Rams Head On Stage 8 Aug 2026

Cyril Neville

Rams Head On Stage - Annapolis 20 Sep 2026

The Buena Vista Orchestra at Rams Head On Stage

Rams Head On Stage 4 Oct 2026

Thursday Night LIVE! Featuring Dan Heely

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

Southern Avenue in Annapolis

Rams Head On Stage 12 Aug 2026

BulletBoys Presented by 97Underground.com Radio

Rams Head On Stage 6 Aug 2026

Mike Dawes

Rams Head On Stage - Annapolis 28 Oct 2026

Lalah Hathaway in Annapolis

Maryland Hall 16 Nov 2026

Thursday Night LIVE! Featuring 8 Ohms

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

Thursday Night LIVE! Featuring The Players Band

307 Sail Pl, Annapolis, MD 21401, United States 27 Aug 2026

Seth Mitchell Band w/ Josh Tobias at 49 West

49 West Coffeehouse, Winebar & Gallery 14 Jul 2026

Old Head: Live on the Red Stage (early + late shows!)

ArtFarm 29 Aug 2026

Matt Schofield

Rams Head On Stage 11 Aug 2026

Blank Page & Chris Diller

Rams Head On Stage 3 Aug 2026

Tuba Skinny

Rams Head On Stage 7 Sep 2026

Seth Kibel Trio - Jazz, Klezmer and more!

49 West Coffeehouse, Winebar & Gallery 26 Jul 2026

All White Dinner Cruise

1 Dock St 30 Aug 2026

Noelle & Jeff Band @Middleton Tavern

Middleton Tavern 7 Aug 2026

Acoustic Alchemy

Rams Head On Stage 20 Oct 2026

CusCampbell

Rams Head On Stage 21 Aug 2026

Young the Giant in Annapolis

Calvert Street Stage 12 Sep 2026

Bountiful Harvest - Costumes & Cocktails

10 Hudson St, Annapolis, MD, United States, Maryland 21401 23 Oct 2026

Royale Lynn at Rams Head On Stage

Rams Head On Stage 16 Jul 2026

Amy Speace in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 15 Jul 2026

Steven Page

Rams Head On Stage - Annapolis 21 Dec 2026

Thursday Night LIVE! Featuring Joe Falero Band

307 Sail Pl, Annapolis, MD 21401, United States 20 Aug 2026

Supernova - A Tribute to Oasis

Rams Head On Stage 13 Aug 2026

Pierce Pettis with Special Guest Danielle Howle in Annapolis

49 West Coffeehouse, Winebar & Gallery 17 Aug 2026

Boney James at Rams Head On Stage

Rams Head On Stage 17 Oct 2026

Karyn Oliver and Miles & Mafale in Annapolis

49 West Coffeehouse, Winebar & Gallery 20 Jul 2026

Jazz Brunch

Captain's Daughter 19 Jul 2026

Charlie Mars and Abe Partridge at Rams Head On Stage

Rams Head On Stage 7 Oct 2026

THE MUSIC AND CRAFTED CULTURE FEST , ANNAPOLIS.

2747 Riva Rd 19 Sep 2026

Candlelight - 90s Unplugged at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 18 Jul 2026

Gaelic Storm at Rams Head On Stage

Rams Head On Stage 4 Nov 2026

Gregg Karukas at Rams Head On Stage

Rams Head On Stage 22 Oct 2026

Marshall Crenshaw with Sarah Borges at Rams Head On Stage

Rams Head On Stage 21 Nov 2026

Laura Brino at Rams Head On Stage

Rams Head On Stage 25 Jul 2026

Lilly Hiatt at Rams Head On Stage

Rams Head On Stage 7 Aug 2026

Mike Love and The Full Circle

Rams Head On Stage 2 Aug 2026

ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026

Jazz and Jams – Natalie Brooke Band with Ahmed Warshanna Trio

801 Chase St, Annapolis, MD, United States, Maryland 21401 16 Aug 2026

Mike Phillips

Rams Head On Stage - Annapolis 30 Aug 2026

Yachtley Crew

Maryland Hall 28 Jul 2026

Halloween Spooktacular!

St. John's College 25 Oct 2026

RICKSHAW LIZARD live on the Harbor Queen!

Watermark Cruises 28 Aug 2026

Peppino D'Agostino in Annapolis

House Concerts 30 Oct 2026

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 28 Aug 2026

Gregg Karukas in Annapolis

Rams Head On Stage 22 Oct 2026

Rachael & Vilray, Taylor Ashton in Annapolis

Rams Head On Stage 10 Dec 2026

The Buena Vista Orchestra

Rams Head On Stage - Annapolis 4 Oct 2026

Dan & Sara - Acoustic Duo - Middleton Tavern Debut!

Middleton Tavern 14 Jul 2026

Old Pine Trio - Rooftop Show at Metropolitan Kitchen and Lounge - July 31st

Metropolitan Kitchen and Lounge 31 Jul 2026

Hyland Brothers Live @ Annapolis Yacht Club

Annapolis Yacht Club 7 Aug 2026

Herman's Hermits & Peter Noone

Rams Head On Stage 22 Nov 2026

IVY LEAGUE, DOMN, DREAM PUNCH at METROPOLITAN Annapolis

Metropolitan Kitchen & Lounge 17 Jul 2026

AND Creative Film Club (July) - The Golem: How He Came Into the World, 1920

AND Creative Studio 24 Jul 2026

SAT 7/18: Gracie Abrams – Daughter From Hell Album Release Party at Third Eye Music & Video

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 18 Jul 2026

Full Bloom: A Summer Sound Bath for What Is Already Yours

333 Dubois Rd 18 Jul 2026

Bonnie Stewart & Maddie Lenhart (matinee)

Rams Head On Stage 9 Aug 2026

🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷

7 Church Cir, Annapolis, MD, United States, Maryland 21401 10 Jun 2026

AND Creative Film Club (June) - El Topo (1970)

AND Creative Studio 26 Jun 2026

Justin Taylor | Annapolis MD

307 Sail Pl Annapolis MD 21401 13 Aug 2026

PMA Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 6 Sep 2026

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis 29 Aug 2026