Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

Maryland Day Celebration 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Across Annapolis & Anne Arundel County, MD, United States, Maryland

Chesapeake Winter Bluegrass FESTIVAL

 Fri, 30 Jan at 12:00 pm Crowne Plaza Annapolis

Historic Annapolis Maryland Day Celebrations

 Sat, 21 Mar at 10:00 am 99 Main Street, Annapolis, MD, United States, Maryland 21401

The Young Fables in Annapolis, MD

 Fri, 20 Feb at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Burning Witches

 Tue, 31 Mar at 07:00 pm Rams Head On Stage

Annapolis Color Run By Color Craze

 Sat, 09 May at 12:00 pm Downtown Annapolis

Sip & Shuck Kick-Off

 Tue, 10 Feb at 03:30 pm Forward Brewing

Stand Up Comedy Night at The Lounge @ Stan and Joe's Saloon

 Fri, 20 Feb at 07:00 pm Stan & Joe's Saloon USD 23

Historic Annapolis Celebrates Maryland Day 2026

 Fri, 20 Mar at 10:00 am Historic Annapolis

Annapolis First Sunday Arts Festival

Sun, 03 May at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

 Mon, 20 Apr at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Honey Sol at Admirals Cup Annapolis

Fri, 06 Feb at 07:00 pm Annapolis, Annapolis, Maryland

Songbird Festival 2026

 Sun, 03 May at 10:00 am Maryland Hall Free

Annapolis Book Festival

 Sat, 02 May at 10:00 am The Key School

High Point Panthers at Navy Midshipmen Mens Lacrosse

 Sat, 31 Jan at 05:00 pm Navy-Marine Corps Memorial Stadium

Jonathan Sloane in Annapolis, MD

 Mon, 15 Jun at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Burning Witches

 Wed, 01 Apr at 08:00 pm Rams Head On Stage