Annapolis Festivals Events

Annapolis Sailboat Show - October 2026

Annapolis City Dock 15 Oct 2026

Kiefer Sutherland ft. Rocco DeLuca: Love Will Bring You Home

Rams Head On Stage 16 Jun 2026

Premier Lacrosse League - All Star at Navy Marine Corps Memorial Stadium

Navy Marine Corps Memorial Stadium 5 Jul 2026

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival

Naval-Marine Corps Stadium 30 May 2026

Premier Lacrosse League - All-Star Games

Navy-Marine Corps Memorial Stadium 5 Jul 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

Annapolis First Sunday Arts Festival

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

Shovels & Rope in Annapolis

Rams Head On Stage 10 Jul 2026

THE ANNAPOLIS SOLSTICE MUSIC AND CRAFT FESTIVAL

2747 Riva Rd 13 Jun 2026

Stand Up Comedy Night at The Lounge @ Stan and Joe's Saloon - TWO SHOWS!

Stan & Joe's Saloon 15 May 2026

Annapolis Open Market Festival

Quiet Waters Park 13 Jun 2026

Naptown Flea

24 Market Space 14 Jun 2026

Annapolis Powerboat Show - Saturday

Annapolis City Dock 16 Oct 2026

Annapolis Water Lantern Festival by Light The Night

Annapolis, Annapolis, Maryland 6 Jun 2026

Michael Cleveland in Annapolis

Annapolis Baygrass Music Festival 20 Sep 2026

Old 4th Ward Unity Day 2026

The People's Park ( Clavert Street and Clay Street Annapolis.MD 21401 27 Jun 2026

Annapolis Color Run By Color Craze

Downtown Annapolis 9 May 2026

2026 Lab Rescue DogWalk & FunFest

Quiet Waters Park Rd, Annapolis, MD 21403, United States 20 Jun 2026

Delegate Bagnall @ Cape St. Claire Strawberry Festival!

Cape St. Claire Improvement Association 6 Jun 2026

Indigenous

Rams Head On Stage 22 May 2026

DCI Annapolis at Navy Marine Corps Memorial Stadium

Navy Marine Corps Memorial Stadium 28 Jul 2026

Eastport a rockin Annapolis

Annapolis Maritime Museum & Park 27 Jun 2026

Annapolis Color Run By Color Craze

Annapolis Landing, Maryland 12 Sep 2026

PMA Unplugged at First Sunday Arts Festival

First Sunday Arts Festival 7 Jun 2026

Pete Yorn Solo Acoustic: 25th Anniversary of musicforthemorningafter

Rams Head On Stage 3 Jun 2026

Jonathan Sloane in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 15 Jun 2026

Black Vending Event

273 Hilltop Ln, Annapolis, MD 21403, United States 9 May 2026

Amy Speace in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 15 Jul 2026

Mac Heat @ First Sunday Arts Festival

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

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

49 West Coffeehouse, Winebar & Gallery 19 Oct 2026