Contests Events in Annapolis

Check out happening contests events all around Annapolis, MD

Annapolis Skelly Run

Sat, 04 Oct at 08:00 pm Annapolis, Annapolis, Maryland

The Australian Bee Gees

Sat, 04 Oct at 07:00 pm Rams Head On Stage

Crack the Sky at Rams Head On Stage

Fri, 31 Oct at 08:00 pm Rams Head On Stage

Taylor Swift The Life of A Showgirl Album Drop Party

Fri, 03 Oct at 04:30 pm Prism Annapolis USD 45

Cruise to St. Michaels OysterFest

Sat, 25 Oct at 09:15 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Keb Mo at Maryland Hall for the Creative Arts

Fri, 21 Nov at 08:00 pm Maryland Hall for the Creative Arts

Ketch Secor

Sun, 02 Nov at 07:00 pm Rams Head On Stage

Haunted Harbour Day 2025

Sat, 25 Oct at 10:00 am 2512 A Solomons Island Road, Annapolis, MD 21401

The Ocean Blue & Brian Tighe of The Hang Ups

Wed, 08 Oct at 07:00 pm Rams Head On Stage

GA20 at Rams Head On Stage

Thu, 23 Oct at 08:00 pm Rams Head On Stage

Lori McKenna

Fri, 03 Oct at 07:00 pm Rams Head On Stage

Cruise to OysterFest in St. Michaels

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

Giselle at Maryland Hall for the Creative Arts

Fri, 17 Oct at 07:30 pm Maryland Hall for the Creative Arts

Chris Isaak at Maryland Hall for the Creative Arts

Sun, 07 Dec at 08:00 pm Maryland Hall for the Creative Arts

Pete Correale

Thu, 06 Nov at 07:00 pm Rams Head On Stage

Tab Benoit at Rams Head On Stage

Sun, 07 Dec Rams Head On Stage

Marshall Crenshaw

Thu, 13 Nov at 07:00 pm Rams Head On Stage

IGNITE Annapolis

Tue, 21 Oct at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

2025 Shore Party

Sat, 01 Nov at 05:00 pm Safe Harbor Annapolis

Annapolis Chocolate Binge Festival

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

Halloween Ghost Hunt in Annapolis

Thu, 30 Oct at 05:00 pm 40 Francis St USD 13 to 40

Carbon Leaf: 'I Want To Be Leaf' Tour 2025

Sat, 13 Dec at 08:30 pm Rams Head On Stage

A Peter White Christmas at Rams Head On Stage

Thu, 04 Dec at 06:30 pm Rams Head On Stage

Sacred Spaces Artist Talk: Featuring Jabari Jefferson & Rush Baker IV

Sat, 11 Oct at 01:00 pm 84 Franklin St, Annapolis, MD, United States, Maryland 21401

Halloween Spooktacular! - October 19, 2025

Sun, 19 Oct at 03:00 pm St. John's College USD 0 to 28

Pure Prairie League at Rams Head On Stage

Fri, 05 Dec at 08:00 pm Rams Head On Stage

Richard Thompson at Francis Scott Key Auditorium at St. John's College

Sun, 02 Nov at 07:30 pm Francis Scott Key Auditorium at St. John's College

Atlanta Rhythm Section

Fri, 05 Dec at 07:00 pm Rams Head On Stage

Shakey Graves

Sat, 13 Dec Rams Head On Stage

Carbon Leaf: Carbon Leaf: 'I Want To Be Leaf' Tour 2025

Sat, 13 Dec at 03:30 pm Rams Head On Stage

Carbon Leaf: 'I Want To Be Leaf' Tour 2025

Sun, 14 Dec at 01:00 pm Rams Head On Stage

Tom Sandoval at Rams Head On Stage

Tue, 30 Sep at 08:00 pm Rams Head On Stage

After Dark Ghost Hunt in Annapolis: Face the Fright!

Wed, 10 Sep at 06:00 pm 40 Francis St USD 10 to 20

Ghosts of Annapolis: Join the Hunt!

Fri, 05 Sep at 05:00 pm 40 Francis St USD 10 to 20

Bacon Brothers at Maryland Hall for the Creative Arts

Thu, 22 Jan at 08:00 pm Maryland Hall for the Creative Arts

The Empty Pockets

Tue, 02 Dec at 07:00 pm Rams Head On Stage

Micky Dolenz at Rams Head On Stage

Tue, 04 Nov at 08:00 pm Rams Head On Stage

Jim Messina at Rams Head On Stage

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

Crack The Sky

Thu, 30 Oct at 07:00 pm Rams Head On Stage

Annapolis Ghost Hunt

Fri, 05 Sep at 04:00 pm 40 Francis St USD 10 to 20

Katie Pruitt

Tue, 14 Oct at 07:00 pm Rams Head On Stage

Iam Tongi at Rams Head On Stage

Tue, 28 Oct at 08:00 pm Rams Head On Stage