Annapolis Festivals Events

Festivals Happening Next in Annapolis, MD

Maryland Day Celebration 2026 - filled with fun events!

 Across Annapolis & Anne Arundel County, MD, United States, Maryland 19 Mar 2026

Chesapeake Winter Bluegrass FESTIVAL

 Crowne Plaza Annapolis 30 Jan 2026
FESTIVALS

The Young Fables in Annapolis, MD

 49 West Coffeehouse, Winebar & Gallery 20 Feb 2026
ENTERTAINMENT USD 23

Historic Annapolis Maryland Day Celebrations

 99 Main Street, Annapolis, MD, United States, Maryland 21401 21 Mar 2026

Burning Witches

 Rams Head On Stage 31 Mar 2026
TRIPS-ADVENTURES

Annapolis Color Run By Color Craze

 Downtown Annapolis 9 May 2026
FESTIVALS

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

 Stan & Joe's Saloon 20 Feb 2026
COMEDY USD 23

Sip & Shuck Kick-Off

 Forward Brewing 10 Feb 2026

Historic Annapolis Celebrates Maryland Day 2026

 Historic Annapolis 20 Mar 2026

Annapolis First Sunday Arts Festival

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

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

 49 West Coffeehouse, Winebar & Gallery 20 Apr 2026
MUSIC USD 23

Honey Sol at Admirals Cup Annapolis

Annapolis, Annapolis, Maryland 6 Feb 2026

Songbird Festival 2026

 Maryland Hall 3 May 2026
FESTIVALS FREE

Jonathan Sloane in Annapolis, MD

 49 West Coffeehouse, Winebar & Gallery 15 Jun 2026
MUSIC USD 23

Annapolis Book Festival

 The Key School 2 May 2026
FESTIVALS

Burning Witches

 Rams Head On Stage 1 Apr 2026