Annapolis Festivals Events

Annapolis Sailboat Show - October 2026

Annapolis City Dock 15 Oct 2026

Annapolis First Sunday Arts Festival

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

Annapolis Powerboat Show - Saturday

Annapolis City Dock 16 Oct 2026

Navy Midshipmen Football vs. Temple Owls Football

Navy Marine Corps Memorial Stadium 7 Nov 2026

St. John’s Block Party

970 St. John’s Drive, Annapolis, MD 21409 24 Oct 2026

Fall Fest

Alder Rd, Annapolis, MD 21402, United States 23 Oct 2026

Annapolis Chocolate Binge Festival

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

8 Ohms Band w/ The G Method

Rams Head On Stage 28 Nov 2026

ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

RICKSHAW LIZARD live at DragonFest - breast cancer benefit!

Pier 4 Marina 17 Oct 2026

PMA at Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 1 Nov 2026

Day of the Dead - Día de los Muertos

Maryland Hall 31 Oct 2026

Annapolis First Sunday Arts Festival w/ The Accidental Poet!!

West St, Annapolis, MD 21401, United States 1 Nov 2026

The Great Annapolis Gingerbread Houses Contest

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

G. Love & Special Sauce - Yeah, It’s That Easy 30th Anniversary Tour

Rams Head On Stage 26 Jan 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