Annapolis Live Music Events

2026 Maryland Seafood Festival

Sandy Point State Park East Beach 12 Sep 2026

Candlelight: 90s Unplugged

Maryland Hall 29 Oct 2026

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 11 Dec 2026

Lalah Hathaway at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 16 Nov 2026

Michael Franti Trio

Rams Head On Stage 28 Sep 2026

Candlelight: A Haunted Evening of Halloween Classics

Maryland Hall 29 Oct 2026

Los Lonely Boys

Rams Head On Stage 28 Sep 2026

Los Lonely Boys at Rams Head On Stage

Rams Head On Stage 29 Sep 2026

Jimmy Charles w. Melissa Quinn Fox

Rams Head On Stage 15 Aug 2026

Carbon Leaf

Rams Head On Stage 11 Dec 2026

Candlelight: Coldplay & Imagine Dragons

Maryland Hall 21 Nov 2026

Jesse Cook in Annapolis

Rams Head On Stage 17 Nov 2026

In Gratitude: A Tribute to Earth, Wind & Fire

Rams Head On Stage 14 Aug 2026

PJ Morton

Rams Head On Stage - Annapolis 4 Aug 2026

Valerie June in Annapolis

Maryland Hall 13 Sep 2026

Phil Vassar (9:30PM)

Rams Head On Stage 23 Oct 2026

Pam Tillis

Rams Head On Stage 16 Aug 2026

Ari Hest at 49 West in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 16 Nov 2026

Digable Planets in Annapolis

Maryland Hall 5 Aug 2026

Southern Culture On the Skids at Rams Head On Stage

Rams Head On Stage 26 Sep 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

Candlelight: Queen vs. The Beatles

Maryland Hall 21 Nov 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

Annapolis First Sunday Arts Festival

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

Michael Cleveland in Annapolis

Annapolis Baygrass Music Festival 20 Sep 2026

The Record Company

Rams Head On Stage 16 Aug 2026

The Record Company at Rams Head On Stage

Rams Head On Stage 17 Aug 2026

Crack the Sky

Rams Head On Stage 31 Oct 2026

Crack the Sky at Rams Head On Stage

Rams Head On Stage 30 Oct 2026

Valerie June

Maryland Hall For The Creative Arts 13 Sep 2026

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

Rams Head On Stage 20 Aug 2026

Candlelight: 90s Unplugged | Annapolis

Maryland Hall 29 Oct 2026

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

Rams Head On Stage 8 Aug 2026

The Buena Vista Orchestra at Rams Head On Stage

Rams Head On Stage 4 Oct 2026

Southern Avenue in Annapolis

Rams Head On Stage 12 Aug 2026

Lalah Hathaway in Annapolis

Maryland Hall 16 Nov 2026

Cyril Neville

Rams Head On Stage - Annapolis 20 Sep 2026

Candlelight: 90s Unplugged

Maryland Hall For The Creative Arts 29 Oct 2026

Mike Dawes

Rams Head On Stage - Annapolis 27 Oct 2026

BulletBoys Presented by 97Underground.com Radio

Rams Head On Stage 6 Aug 2026

Sean Hayes w/ Etienne de Rocher (Haunted Shed)

Rams Head On Stage 23 Sep 2026

Deer Tick at Rams Head On Stage

Rams Head On Stage 18 Nov 2026

Blank Page & Chris Diller

Rams Head On Stage 3 Aug 2026

Tuba Skinny

Rams Head On Stage 7 Sep 2026

Official Annapolis Baygrass Kick-Off Party w/ Jammy Buffet

Maryland Hall 18 Sep 2026

Mel Brooks’ Young Frankenstein

143 Compromise St, Annapolis, MD, United States, Maryland 21401 6 Aug 2026

Thursday Night LIVE! Featuring 8 Ohms

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

John Splithoff in Annapolis

Rams Head On Stage 21 Nov 2026

Matt Schofield

Rams Head On Stage 11 Aug 2026

Thursday Night LIVE! Featuring The Players Band

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

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

ArtFarm 29 Aug 2026

Pops in the Park at Quiet Waters Park

Quiet Waters Park Rd, Annapolis, MD 21403, United States 6 Sep 2026

AMFM Presents: In The Vane of Billy Joel

Rams Head On Stage 14 Sep 2026

All White Dinner Cruise

1 Dock St 30 Aug 2026

Gregg Karukas in Annapolis

Rams Head On Stage 22 Oct 2026

Steven Page

Rams Head On Stage - Annapolis 21 Dec 2026

Noelle & Jeff Band @Middleton Tavern

Middleton Tavern 7 Aug 2026

Wine Down at the Farm

Historic Goshen Farm & Educational Center 29 Aug 2026

RICKSHAW LIZARD live on the Harbor Queen!

Watermark Cruises 28 Aug 2026

Boney James

Rams Head On Stage 17 Oct 2026

CusCampbell

Rams Head On Stage 21 Aug 2026

Acoustic Alchemy

Rams Head On Stage 20 Oct 2026

Bountiful Harvest - Costumes & Cocktails

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

Supernova - A Tribute to Oasis

Rams Head On Stage 13 Aug 2026

THE MUSIC AND CRAFTED CULTURE FEST , ANNAPOLIS.

2747 Riva Rd 19 Sep 2026

Pierce Pettis with Special Guest Danielle Howle in Annapolis

49 West Coffeehouse, Winebar & Gallery 17 Aug 2026

Thursday Night LIVE! Featuring Joe Falero Band

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

Patti Smith in Annapolis

Maryland Hall 2 Sep 2026

Mike Phillips

Rams Head On Stage - Annapolis 30 Aug 2026

Boney James at Rams Head On Stage

Rams Head On Stage 17 Oct 2026

Charlie Mars and Abe Partridge at Rams Head On Stage

Rams Head On Stage 7 Oct 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

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

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026

The Buena Vista Orchestra

Rams Head On Stage - Annapolis 4 Oct 2026

Play A Song Second Annual Music Festival

Eastport Democratic Club 4 Oct 2026

Lilly Hiatt at Rams Head On Stage

Rams Head On Stage 7 Aug 2026

Marshall Crenshaw with Sarah Borges at Rams Head On Stage

Rams Head On Stage 21 Nov 2026

Create & Paddle with Honey Creative Hive

680 Americana Drive, Annapolis, MD, United States, Maryland 21403 4 Aug 2026

Rick Braun in Annapolis

Rams Head On Stage 15 Nov 2026

Jazz and Jams – Natalie Brooke Band with Ahmed Warshanna Trio

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

Valerie June w/ Judy Blank

801 Chase St, Annapolis, MD 21401-3530, United States 13 Sep 2026

Halloween Spooktacular!

St. John's College 25 Oct 2026

Peppino D'Agostino in Annapolis

House Concerts 30 Oct 2026

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

Maryland Hall for the Creative Arts 29 Oct 2026

Rachael and Vilray at Rams Head On Stage

Rams Head On Stage 10 Dec 2026

Acoustic Alchemy at Rams Head On Stage

Rams Head On Stage 20 Oct 2026

🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷

7 Church Cir, Annapolis, MD, United States, Maryland 21401 5 Aug 2026

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 28 Aug 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

Bonnie Stewart & Maddie Lenhart (matinee)

Rams Head On Stage 9 Aug 2026

Charlene Kaye at Rams Head On Stage

Rams Head On Stage 28 Oct 2026

Justin Taylor | Annapolis MD

307 Sail Pl Annapolis MD 21401 13 Aug 2026

Mac Heat @ First Sunday Arts Festival

West St, Annapolis, MD 21401, United States 4 Oct 2026

Ocean Pain Live! For Our Sober Friends

2016 Industrial Dr, Annapolis, MD 21401-4699, United States 29 Aug 2026

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

Charthouse Restaurant Annapolis 29 Aug 2026

AND Creative Film Club (August) - a Kim Merced Garland Film Retrospective

AND Creative Studio 28 Aug 2026

Mac Heat @ Annapolis Smokehouse & Tavern

Annapolis Smokehouse and Tavern 25 Sep 2026