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Events in Annapolis, MD

GrindKit tracks 26 festivals, markets, and vendor opportunities in Annapolis. Built for mobile coffee, food, and beverage operators.

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Upcoming (19)

Dec 6, 2026
Annapolis Chocolate Festival
Community
Dec 6, 2026
Annapolis Chocolate Binge Festival
Community
Dec 13-21, 2026
Annapolis Holiday Market
Markets
Dec 19, 2026
Naptown Half Marathon, 10K & 5K
Sports
Dec 19, 2026
Naptown Half Marathon, 10K & 5K - Holiday Hustle
Sports
Jan 15, 2027
Annapolis Opry – An Acoustic Concert Series
Community
Jan 17, 2027
United States Army Jazz Band - Jazz Ambassadors Concert
Community
Jan 17, 2027
United States Army Jazz Band - Jazz Ambassadors
Community
Jan 17, 2027
United States Army Jazz Band (Jazz Ambassadors)
Community
Feb 3, 2027
Cécile McLorin Salvant and Glenn Zaleski Concert
Community
Feb 3, 2027
Cécile McLorin Salvant and Glenn Zaleski
Community
Feb 10, 2027
Annapolis Opera Presents: The Ugly Duckling - A Children's Opera
Community
Feb 10, 2027
Annapolis Opera Presents: The Ugly Duckling: A Children's Opera
Community
Feb 21, 2027
Maryland Hall Presents: Ami Dang
Community
Mar 20, 2027
Annapolis Running Festival
Sports
Mar 20, 2027
Oyster Roast and Sock Burning
Community
Jul 19, 2027
Endless Summer Six-Hour Run
Sports
May 28 – May 29, 2027
Annapolis Irish Festival
Community
Date TBA
Annapolis Memorial Day Parade
Festivals

Past (7)

Aug 29 – Oct 25, 2026
Maryland Renaissance Festival
Community
Aug 30, 2026
Annapolis Ten Mile Run
Sports
Sep 12-13, 2026
Maryland Seafood Festival
Vendor Apps
Sep 19-20, 2026
Annapolis Baygrass Music Festival
Festivals
Sep 20, 2026
Annapolis RUN for The Light House
Sports
Nov 8, 2026
Chesapeake Bay Bridge Run
Sports
Nov 8, 2026
Bay Bridge Run
Sports