Annapolis Festivals Events

Annapolis Sailboat Show - October 2026

Annapolis City Dock 15 Oct 2026

2026 Maryland Seafood Festival

Sandy Point State Park East Beach 12 Sep 2026

Nitro Circus Live at Navy Marine Corps Memorial Stadium

Navy Marine Corps Memorial Stadium 23 Aug 2026

BAYGRASS 2026: Annapolis Baygrass Music Festival 9/19-20

1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 19 Sep 2026

Navy Midshipmen Football vs. Temple Owls Football

Navy Marine Corps Memorial Stadium 7 Nov 2026

21st Annual Boatyard Beach Bash

723 2nd St, Annapolis, MD, United States, Maryland 21403 19 Sep 2026

36th Annual Kunta Kinte Heritage Festival

Navy–Marine Corps Memorial Stadium 26 Sep 2026

Comedian Josh Blue of Last Comic Standing

Rams Head On Stage 15 Oct 2026

The Peake Run- Our Big Ducking Run to Celebrate the 60 Years of the Maryland Seafood Festival

Sandy Point State Park 13 Sep 2026

Annapolis First Sunday Arts Festival

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

Free Back to School Events

2323 Forest Dr, Annapolis, MD, United States, Maryland 21401 20 Aug 2026

Michael Cleveland in Annapolis

Annapolis Baygrass Music Festival 20 Sep 2026

Jim's Marine at the Annapolis Powerboat Show

Annapolis City Dock 8 Oct 2026

Annapolis Powerboat Show - Saturday

Annapolis City Dock 16 Oct 2026

Peter Levin (Gregg Allman’s Keyboard Player) with The Fitzkee Brothers

Rams Head On Stage 8 Aug 2026

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews (7:30PM)

Rams Head On Stage 11 Oct 2026

Official Annapolis Baygrass Kick-Off Party w/ Jammy Buffet

Maryland Hall 18 Sep 2026

All You Need w/ Skribe

Rams Head On Stage 23 Aug 2026

Matt Schofield

Rams Head On Stage 11 Aug 2026

Maryland Renaissance Festival - Photo Meetup 2026

Maryland Renaissance Festival 26 Sep 2026

Laughs in the Lounge

Stan & Joe's Saloon 18 Sep 2026

Annapolis Color Run By Color Craze

Annapolis Landing, Maryland 12 Sep 2026

LOVE SPORTS’ Love Fest 2026 | Free Family Festival

215 Croll drive 15 Aug 2026

2026 Drug Education & Awareness Sporting Festival

Annapolis Recreation & Parks 12 Sep 2026

THE MUSIC AND CRAFTED CULTURE FEST , ANNAPOLIS.

2747 Riva Rd 19 Sep 2026

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

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026

Play A Song Second Annual Music Festival

Eastport Democratic Club 4 Oct 2026

The Taste: Celebrate the Chesapeake in Maryland

The Atreeum at Soaring Timbers 24 Sep 2026

Walt Wilkins and Marc Douglas Berardo in Annapolis

49 West Coffeehouse, Gallery and Winebar 23 Sep 2026

Navy Football Fan Fest 2026

Navy–Marine Corps Memorial Stadium 8 Aug 2026

Gold Leaf x Pink Planes Presents High Society Weekend

GOLDLEAF 14 Aug 2026

Fall Saturdays at Ridge Grow

244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 12 Sep 2026

Mac Heat @ First Sunday Arts Festival

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

AND Creative Film Club (August) - a Kim Merced Garland Film Retrospective

AND Creative Studio 28 Aug 2026

PMA Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 6 Sep 2026

Cape Conservation Corps Native Plant Fest and Sale

1223 River Bay Rd annapolis 26 Sep 2026

PMA at Annapolis Chocolate Binge Festival

Annapolis West Street 6 Dec 2026