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

Eastport a Rockin' 2026

 Sat, 27 Jun at 11:00 am 701 2nd St, Annapolis, MD, United States, Maryland 21403

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

Nitro Circus Live at Navy Marine Corps Memorial Stadium

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

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

 Sat, 19 Sep at 02:00 pm 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

Eastport Rockin' Festival, Annapolis, MD

 Sat, 27 Jun at 02:45 pm 105 Eastern Ave, Annapolis, MD 21403-3300, United States

Carr's Beach Reunion: Juneteenth Celebration

 Fri, 19 Jun at 03:00 pm Annapolis Maritime Museum

Premier Lacrosse League - All-Star Games

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

Navy Midshipmen Football vs. Temple Owls Football

 Sat, 13 Jun at 06:00 pm Navy Marine Corps Memorial Stadium

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

Annapolis First Sunday Arts Festival

Sun, 03 May Calvert and West Streets, 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

DCI Annapolis at Navy Marine Corps Memorial Stadium

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

Annapolis Open Market Festival

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

Naptown Flea

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

Laughs in the Lounge

 Fri, 12 Jun at 07:00 pm Stan & Joe's Saloon USD 23

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

City Dock Tango at Arts Annapolis 2026

 Sat, 13 Jun at 04:00 pm Calvert St and West St, Annapolis

Lilly Hiatt Band

 Fri, 07 Aug at 08:00 pm Rams Head On Stage

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

 Thu, 11 Jun TGI Fridays Free

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

Ghalia Volt w. Kent Burnside

Tue, 25 Aug at 08:00 pm Rams Head On Stage

Annapolis Color Run By Color Craze

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

Jonathan Sloane in Annapolis, MD

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

Amy Speace in Annapolis, MD

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

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

Karyn Oliver and Miles & Mafale in Annapolis

 Mon, 20 Jul at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Walt Wilkins and Marc Douglas Berardo in Annapolis

 Wed, 23 Sep at 08:00 pm 49 West Coffeehouse, Gallery and Winebar USD 23

PMA Unplugged at First Sunday Arts Festival

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

The Black Feathers in Annapolis, MD

 Wed, 17 Jun at 08:00 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

Mystic Kirtan by Mirabai Moon

Sat, 11 Jul at 07:00 pm 4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409

1st Sunday June Open Beach Jam

 Sun, 07 Jun at 04:00 pm Lake Claire

Here's to Heroes!

Tue, 07 Jul at 10:00 am 155 Main St, Annapolis, MD, United States, Maryland 21401