Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

Annapolis Chocolate Binge Festival

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

The Great Annapolis Gingerbread Houses Contest

 Sat, 22 Nov at 03:00 pm 26 West St, Annapolis, MD 21401-2421, United States

Sister Hazel (matinee)

Sat, 15 Nov at 01:00 pm Rams Head On Stage

The Carole King & James Taylor Story

 Sat, 15 Nov at 08:00 pm Rams Head On Stage

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

 Sat, 15 Nov at 07:00 pm Stan & Joe's Saloon USD 23

The Doug Segree Band at 49 West

Mon, 17 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

U2topia: The Mid-Atlantic U2 Tribute Band

Fri, 28 Nov at 08:00 pm Rams Head On Stage

Deadgrass, Bluegrass Covers of The Grateful Dead

 Tue, 11 Nov at 07:30 pm Annapolis Mall USD 34

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

 Fri, 14 Nov at 07:00 pm Stan & Joe's Saloon USD 23

Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"

 Sat, 15 Nov at 11:00 am Anne Arundel County Public Library (Eastport-Annapolis Neck Library)

PARKING: Military Bowl

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

Joshua Redman Quartet

 Sun, 16 Nov at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

Pressing Strings

 Sun, 28 Dec at 08:00 pm Rams Head On Stage

The Empty Pockets at Rams Head On Stage

 Wed, 03 Dec at 08:00 pm Rams Head On Stage

Annual Kwanzaa Celebration

 Sat, 13 Dec at 10:00 am 84 Franklin St, Annapolis, MD, United States, Maryland 21401

Annapolis Jazz & Roots Festival Freedom Choir led by Elizabeth Melvin

 Sun, 16 Nov at 03:00 pm St. Luke's Eastport

Annapolis Color Run By Color Craze

 Sat, 09 May at 12:00 pm Downtown Annapolis

Parking Military Bowl

 Sat, 27 Dec at 04:00 pm Navy-Marine Corps Memorial Stadium

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews (Matinee Added By Popular Demand!)

 Sun, 16 Nov at 01:00 pm Rams Head On Stage

Maryland Day Week 2026 - filled with fun events!

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

Burning Witches

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

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100