Annapolis Festivals Events

Navy Midshipmen Football vs. Temple Owls Football

Navy Marine Corps Memorial Stadium 7 Nov 2026

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 6 Dec 2026

Mad Cute Market 🍂 Gilmore Girls Autumn

730 Bestgate Rd 20 Nov 2026

8 Ohms Band w/ The G Method

Rams Head On Stage 28 Nov 2026

National Pupusa Day — Weekend Celebration!

Caliente Grill 6 Nov 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Laughs in the Lounge

Stan & Joe's Saloon 13 Nov 2026

Ribbon Cutting for 6th Street Waterfront Park

6th Street Street-end Park 6 Nov 2026

The Great Annapolis Gingerbread Houses Contest

26 West St, Annapolis, MD 21401-2421, United States 22 Nov 2026

Winter Wonderjam

Dark Horse Annapolis 28 Nov 2026

1776: Yuletide in Revolutionary Annapolis

186 Prince George St, Annapolis, MD 21401-1724, United States 5 Dec 2026

Amelia White and Meg Murray in Annapolis

49 West Coffeehouse, Winebar & Gallery 15 Mar 2027

PMA at Annapolis Chocolate Binge Festival

Annapolis West Street 6 Dec 2026

Annapolis Jazz and Roots Festival - Muneer Nasser Band Jazz Genius: Coltrane, Miles & Weston ​

St. Luke's Eastport 6 Nov 2026

Annapolis Jazz and Roots Festival - Music for Lafayette: 1770s -1820s

Unitarian Universalist Church of Annapolis 8 Nov 2026