Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

Annapolis Sailboat Show - October 2026

 Thu, 15 Oct at 09:00 am Annapolis City Dock

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

 Tue, 16 Jun at 08:00 pm Rams Head On Stage

Nitro Circus Live at Navy Marine Corps Memorial Stadium

 Sun, 23 Aug Navy Marine Corps Memorial Stadium

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

 Sun, 05 Jul Navy Marine Corps Memorial Stadium

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

 Sat, 19 Sep at 10:00 am 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

Shovels & Rope in Annapolis

 Fri, 10 Jul at 08:00 pm Rams Head On Stage

Annapolis First Sunday Arts Festival

Sun, 03 May at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Premier Lacrosse League - All-Star Games

 Sun, 05 Jul at 06:00 pm Navy-Marine Corps Memorial Stadium

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival

 Sat, 30 May at 02:00 pm Naval-Marine Corps Stadium USD 0 to 82

Children's Day Festival - Free Family Friendly Event

 Sat, 02 May at 12:00 pm 25 Silopanna Rd, Annapolis, MD, United States, Maryland 21403

THE ANNAPOLIS SOLSTICE MUSIC AND CRAFT FESTIVAL

 Sat, 13 Jun at 10:00 am 2747 Riva Rd Free

West Annapolis May Day Market

 Sun, 26 Apr at 11:00 am Annapolis Street, Annapolis, MD, United States, Maryland 21401

Annapolis Powerboat Show - Saturday

 Fri, 16 Oct at 07:00 pm Annapolis City Dock

Michael Cleveland in Annapolis

 Sun, 20 Sep at 07:00 pm Annapolis Baygrass Music Festival

Annapolis Spring Italian Festa

 Sun, 26 Apr at 10:00 am 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401

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

 Fri, 15 May at 07:00 pm Stan & Joe's Saloon USD 23

Annapolis Color Run By Color Craze

 Sat, 09 May at 12:00 pm Downtown Annapolis

Annapolis Water Lantern Festival by Light The Night

 Sat, 06 Jun at 06:30 pm Annapolis, Annapolis, Maryland

DCI Annapolis at Navy Marine Corps Memorial Stadium

 Tue, 28 Jul at 11:59 pm Navy Marine Corps Memorial Stadium

Eastport a rockin Annapolis

Sat, 27 Jun at 04:30 pm Annapolis Maritime Museum & Park

Old 4th Ward Unity Day 2026

Sat, 27 Jun at 05:00 pm The People's Park ( Clavert Street and Clay Street Annapolis.MD 21401

Delegate Bagnall @ Cape St. Claire Strawberry Festival!

 Sat, 06 Jun at 10:00 am Cape St. Claire Improvement Association

ANNAPOLIS VINTAGE MARKET

Sun, 03 May at 11:00 am 40 Hudson St Unit 107, Annapolis, MD

Annapolis Color Run By Color Craze

 Sat, 12 Sep at 12:00 pm Annapolis Landing, Maryland

Indigenous

 Fri, 22 May Rams Head On Stage

Goshen Farm Family Day

 Sat, 02 May at 10:00 am Historic Goshen Farm & Educational Center

PMA Unplugged at First Sunday Arts Festival

Sun, 07 Jun at 02:00 pm First Sunday Arts Festival

Black Vending Event

Sat, 09 May at 10:00 am 273 Hilltop Ln, Annapolis, MD 21403, United States

Songbird Festival 2026

 Sun, 03 May at 10:00 am Maryland Hall Free

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

 Mon, 19 Oct at 07:30 pm 49 West Coffeehouse, Winebar & Gallery Free

Pete Yorn Solo Acoustic: 25th Anniversary of musicforthemorningafter

Wed, 03 Jun at 08:00 pm Rams Head On Stage

Jonathan Sloane in Annapolis, MD

 Mon, 15 Jun at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Annapolis Striders John Wall Memorial One Mile Track Run 2026

 Sat, 27 Jun at 08:00 am Annapolis High School (Maryland)

Mac Heat @ First Sunday Arts Festival

 Sun, 03 May at 11:00 am Stan and Joe's Saloon

Amy Speace in Annapolis, MD

 Wed, 15 Jul at 08:00 pm 49 West Coffeehouse, Winebar & Gallery USD 23

AUDITIONS — 10-Minute Play Festival

 Sun, 26 Apr at 01:00 pm 2134 Renard Ct, Annapolis, MD 21401-6755, United States

Annapolis Book Festival

 Sat, 02 May at 10:00 am The Key School