Annapolis Festivals Events

Maryland Renaissance Festival at Maryland Renaissance Festival

Maryland Renaissance Festival 27 Sep 2026

Annapolis Sailboat Show - October 2026

Annapolis City Dock 15 Oct 2026

36th Annual Kunta Kinte Heritage Festival

Navy–Marine Corps Memorial Stadium 26 Sep 2026

Annapolis First Sunday Arts Festival

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

Jim's Marine at the Annapolis Powerboat Show

Annapolis City Dock 8 Oct 2026

Maryland Renaissance Festival - Photo Meetup 2026

Maryland Renaissance Festival 26 Sep 2026

Annapolis Powerboat Show - Saturday

Annapolis City Dock 16 Oct 2026

Walt Wilkins and Marc Douglas Berardo in Annapolis

49 West Coffeehouse, Gallery and Winebar 23 Sep 2026

Navy Midshipmen Football vs. Temple Owls Football

Navy Marine Corps Memorial Stadium 7 Nov 2026

The Taste: Celebrate the Chesapeake in Maryland

The Atreeum at Soaring Timbers 24 Sep 2026

Play A Song Second Annual Music Festival

Eastport Democratic Club 4 Oct 2026

Annapolis Chocolate Binge Festival

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

Cape Conservation Corps Native Plant Fest and Sale

1223 River Bay Rd annapolis 26 Sep 2026

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

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026

8 Ohms Band w/ The G Method

Rams Head On Stage 28 Nov 2026

Mac Heat @ First Sunday Arts Festival

West St, Annapolis, MD 21401, United States 4 Oct 2026

PMA at Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 1 Nov 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