Music Festivals in Annapolis

Check out happening music festivals events all around Annapolis, MD

War in Annapolis

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

35th Annual Kunta Kinte Heritage Festival

Sat, 13 Sep at 10:00 am Navy–Marine Corps Memorial Stadium

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

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

Skerryvore in Annapolis

Mon, 08 Sep 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

BAYGRASS 2025: Annapolis Baygrass Music Festival 9/20-21

Sat, 20 Sep at 10:00 am 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

Dirty Heads

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

Dustbowl Revival w/ Chris Kasper

Sun, 07 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

Annapolis Songwriters Festival - Platinum Pass

Thu, 11 Sep at 05:00 pm Rams Head On Stage

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

Casey Abrams & Friends featuring Dylan Chambers and Hunter

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

Old Crow Medicine Show in Annapolis

Mon, 03 Nov at 08:00 pm Rams Head On Stage