Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon

 Sat, 15 Nov at 07:00 pm Stan & Joe's Saloon USD 23

The Doug Segree Band at 49 West

Mon, 17 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

Stand Up Comedy & Music Night at The Lounge @ Stan and Joe's Saloon

 Fri, 14 Nov at 07:00 pm Stan & Joe's Saloon USD 23

Trunk or Treat

 Fri, 24 Oct at 03:30 pm Eucalyptus Rd, Annapolis, MD 21402, United States

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 26 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

SAMHAIN- 2025

 Sat, 01 Nov at 07:00 pm Unitarian Universalist Church of Annapolis

PARKING: Military Bowl

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

The Carole King & James Taylor Story

 Sat, 15 Nov at 08:00 pm Rams Head On Stage

Taste of Fall on West Street

 Sun, 09 Nov at 02:00 pm 53 West St USD 7 to 82

Harvest Festival - FREE

 Sat, 25 Oct at 10:00 am Roger W "Pip" Moyer Community Recreation Center at Truxtun Park, 273 Hilltop Ln, Annapolis, MD, United States, Maryland 21403

Pete Correale at Rams Head On Stage

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

Deadgrass, Bluegrass Covers of The Grateful Dead

 Tue, 11 Nov at 07:30 pm Annapolis Mall USD 34

Sister Hazel (matinee)

Sat, 15 Nov at 01:00 pm Rams Head On Stage

U2topia: The Mid-Atlantic U2 Tribute Band

Fri, 28 Nov at 08:00 pm Rams Head On Stage

2025 Hall & Friends Oyster Roast

 Sat, 01 Nov at 02:00 pm Bay Ridge Marina

Joshua Redman Quartet

 Sun, 16 Nov at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

Annapolis Jazz & Roots Festival - Michael McHenry Tribe

 Sun, 09 Nov at 02:30 pm Pip Moyer Recreation Center at Truxtun Park

The Empty Pockets at Rams Head On Stage

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

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

First Sunday Arts Festival

Sun, 02 Nov at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"

 Sat, 15 Nov at 11:00 am Anne Arundel County Public Library (Eastport-Annapolis Neck Library)

Cruise to OysterFest in St. Michaels

 Sat, 25 Oct at 09:00 am 1 Dock St, Annapolis, MD, United States, Maryland 21401

Annapolis Jazz & Roots Festival JC Jefferson - Salute to Quincy Jones

 Sat, 08 Nov at 02:00 pm Banneker-Douglass-Tubman Museum

Fall Fling With Bling

 Wed, 22 Oct at 11:00 am 2747 Riva Rd Free

Pressing Strings

 Sun, 28 Dec at 08:00 pm Rams Head On Stage

The Great Annapolis Gingerbread Houses Contest

 Sat, 22 Nov at 03:00 pm 26 West St, Annapolis, MD 21401-2421, United States

Annapolis Jazz & Roots Festival "Art Music & the Muse" Artist talk - Jabari and JC Jefferson

 Sat, 08 Nov at 01:00 pm Banneker-Douglass-Tubman Museum

Parking Military Bowl

 Sat, 27 Dec at 04:00 pm Navy-Marine Corps Memorial Stadium

Annapolis Jazz & Roots Festival Alexis Tantau & Letitia VanSant with Rusty Sal - Eva Cassidy Tribute

 Fri, 07 Nov at 05:30 pm Peerless Rens Club

Here's to Heroes!

Tue, 04 Nov at 10:00 am 155 Main St, Annapolis, MD, United States, Maryland 21401

The Young Dubliners: The HOT TODDY Tour

 Tue, 10 Feb at 08:00 pm Rams Head On Stage

Maryland Day Week 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Anne Arundel County, MD, United States, Maryland

Burning Witches

 Tue, 31 Mar at 07:00 pm Rams Head On Stage

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100