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

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

 Sun, 05 Jul Navy Marine Corps Memorial Stadium

Annapolis Blues Home Opener | May 30th

 Sat, 30 May at 05:00 pm Navy-Marine Corps Memorial Stadium

Premier Lacrosse League - All-Star Games

 Sun, 05 Jul at 06:00 pm 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

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

Nitro Circus Live at Navy Marine Corps Memorial Stadium

 Sun, 23 Aug at 06:00 pm Navy Marine Corps Memorial Stadium

Annapolis First Sunday Arts Festival

Sun, 03 May Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Shovels & Rope in Annapolis

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

THE ANNAPOLIS SOLSTICE MUSIC AND CRAFT FESTIVAL

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

Art on the Avenue

 Thu, 04 Jun at 06:00 pm Maryland Avenue Free

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 Open Market Festival

 Sat, 13 Jun at 10:00 am Quiet Waters Park Free

DCI Annapolis at Navy Marine Corps Memorial Stadium

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

Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night

 Thu, 28 May at 08:00 pm TGI Fridays Free

Naptown Flea

 Sun, 14 Jun at 01:00 pm 24 Market Space Free

Annapolis Water Lantern Festival by Light The Night

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

Annapolis Striders Women's Distance Festival 5K 2026

 Sat, 11 Jul at 07:45 am West Annapolis Elementary School, 505 Melvin Avenue, Annapolis, MD 21401

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

Eastport a rockin Annapolis

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

2026 Lab Rescue DogWalk & FunFest

 Sat, 20 Jun at 11:00 am Quiet Waters Park Rd, Annapolis, MD 21403, United States

Delegate Bagnall @ Cape St. Claire Strawberry Festival!

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

Indigenous

 Fri, 22 May Rams Head On Stage

Annapolis Color Run By Color Craze

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

Amy Speace in Annapolis, MD

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

PMA Unplugged at First Sunday Arts Festival

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

Pete Yorn Solo Acoustic: 25th Anniversary of musicforthemorningafter

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

Karyn Oliver and Miles & Mafale in Annapolis

 Mon, 20 Jul 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)

Jonathan Sloane in Annapolis, MD

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

Mac Heat @ First Sunday Arts Festival

 Sun, 04 Oct at 11:00 am West St, Annapolis, MD 21401, United States

Broadneck Library Bluegrass Jam: May and June

 Thu, 28 May at 05:30 pm Anne Arundel County Public Library (Broadneck Library)

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