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

Steve Oliver & The Grainger Brothers

Rams Head On Stage 26 Jul 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

Michael Cleveland in Annapolis

Annapolis Baygrass Music Festival 20 Sep 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

DCI Annapolis at Navy Marine Corps Memorial Stadium

Navy Marine Corps Memorial Stadium 28 Jul 2026

97Underground.com Presents Royale Lynn: The Royale Pain In The A$$ Tour w/ Stone Horses

Rams Head On Stage 16 Jul 2026

Matt Schofield

Rams Head On Stage 11 Aug 2026

All You Need w/ Skribe

Rams Head On Stage 23 Aug 2026

Annapolis Color Run By Color Craze

Annapolis Landing, Maryland 12 Sep 2026

2026 Drug Education & Awareness Sporting Festival

Annapolis Recreation & Parks 12 Sep 2026

Amy Speace in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 15 Jul 2026

Walt Wilkins and Marc Douglas Berardo in Annapolis

49 West Coffeehouse, Gallery and Winebar 23 Sep 2026

Karyn Oliver and Miles & Mafale in Annapolis

49 West Coffeehouse, Winebar & Gallery 20 Jul 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

PMA Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 6 Sep 2026

full moon ecstatic dance

Groundswell yoga shala 29 Jul 2026

Mac Heat @ First Sunday Arts Festival

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

Cape Conservation Corps Native Plant Fest and Sale

1223 River Bay Rd annapolis 26 Sep 2026

Bubble Fest

25 Silopanna Rd, Annapolis, MD, United States, Maryland 21403 18 Jul 2026

PMA at Annapolis Chocolate Binge Festival

Annapolis West Street 6 Dec 2026