Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

The Sergio Mendes Band at Rams Head On Stage

 Fri, 12 Jun Rams Head On Stage

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

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

Thu Apr 30 | Annapolis, MD | 7:00PM | Cirque de Paris

 Thu, 30 Apr at 07:00 pm Under the Big Top! Annapolis Mall USD 34

SAT 4/25/26: Foo Fighters – Your Favorite Toy Album Release Party at Third Eye Music & Video

 Sat, 25 Apr at 07:00 pm 209 chinquapin round rd suite 300, Annapolis, MD, United States, Maryland 21401

Stewart Copeland at Rams Head On Stage

 Tue, 21 Jul Rams Head On Stage

Sun May 10 | Annapolis, MD | 4:30PM | Cirque de Paris

 Sun, 10 May at 04:30 pm Under the Big Top! Annapolis Mall

Fri May 8 | Annapolis, MD | 4:30PM | Cirque de Paris

 Fri, 08 May at 04:30 pm Under the Big Top! Annapolis Mall

Fri May 1 | Annapolis, MD | 7:30PM | Cirque de Paris

 Fri, 01 May at 07:30 pm Under the Big Top! Annapolis Mall USD 34

Sérgio Mendes in Annapolis

 Fri, 12 Jun at 09:00 pm Rams Head On Stage

Al Di Meola Electric Band

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

Mon May 4 | Annapolis, MD | 7:00PM | Cirque de Paris

 Mon, 04 May at 07:00 pm Under the Big Top! Annapolis Mall

Stewart Copeland

 Mon, 20 Jul at 07:00 pm Rams Head On Stage

Sat May 9 | Annapolis, MD | 7:30PM | Cirque de Paris

 Sat, 09 May at 07:30 pm Under the Big Top! Annapolis Mall

Al Jardine and The Pet Sounds Band at Maryland Hall for the Creative Arts

 Thu, 06 Aug at 08:00 pm Maryland Hall for the Creative Arts

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

Cirque de Paris | Annapolis, MD

 Thu, 14 May at 07:00 pm Annapolis Mall

The Smithereens in Annapolis

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

Friends for Friends

 Thu, 14 May at 06:00 pm Fluegel Alumni Center

The Hip Hop R&B Yacht Party Annapolis MD 4.26.26

 Sun, 26 Apr at 04:45 pm Annapolis City Dock USD 79 to 139

The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026

 Sun, 07 Jun at 04:45 pm Annapolis City Dock USD 79 to 139

Sat May 9 | Annapolis, MD | 1:30PM | Cirque de Paris

 Sat, 09 May at 01:30 pm Under the Big Top! Annapolis Mall

Asleep at the Wheel at Rams Head On Stage

 Sat, 16 May at 01:00 pm Rams Head On Stage

Shovels & Rope in Annapolis

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

Robyn Hitchcock at Rams Head On Stage

 Wed, 17 Jun 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

The Smithereens w. Guest Vocalist Marshall Crenshaw

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

The Lone Bellow at Rams Head On Stage

 Sat, 16 May at 08:00 pm Rams Head On Stage

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

Pam Tillis

 Sat, 15 Aug at 07:00 pm Rams Head On Stage

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 Smithereens

 Thu, 04 Jun at 07:00 pm Rams Head On Stage

Marion Meadows, Alex Bugnon in Annapolis

 Fri, 24 Jul at 08:00 pm Rams Head On Stage

Cracker at Rams Head On Stage

 Sun, 14 Jun Rams Head On Stage

The Sergio Mendes Band

 Thu, 11 Jun at 07:00 pm Rams Head On Stage

Los Lonely Boys at Rams Head On Stage

 Tue, 29 Sep at 08:00 pm Rams Head On Stage

Candlelight: 90s Unplugged

 Sat, 18 Jul at 06:45 pm Maryland Hall USD 28 to 69

Alan Doyle

 Wed, 29 Apr at 07:00 pm Rams Head On Stage

Reverend Peyton's Big Damn Band

 Tue, 28 Apr Rams Head On Stage

Graham Parker

 Fri, 01 May at 07:00 pm Rams Head On Stage

Colin James Matt Anderson & Terra Lightfoot

 Tue, 05 May at 07:00 pm Rams Head On Stage

Taste of Spring on West Street 2026

 Sun, 17 May at 01:00 pm 53 West St USD 7 to 82

An Evening with Chris Trapper (Late Show)

 Sat, 25 Apr at 09:00 pm 49 West Coffeehouse, Winebar & Gallery USD 34

Thursday Night LIVE! Featuring The Chucks

 Thu, 11 Jun at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Michael Cleveland in Annapolis

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

The Reverend Peyton's Big Damn Band

 Thu, 30 Apr at 12:00 am Rams Head On Stage - Annapolis

The Golden Girls Murder Mystery

 Sat, 09 May at 01:00 pm Crowne Plaza Annapolis by IHG USD 45 to 65

Andrew Duhon at Rams Head On Stage

 Tue, 26 May Rams Head On Stage

Andrew Duhon

 Mon, 25 May at 07:00 pm Rams Head On Stage

Candlelight: Coldplay & Imagine Dragons Tribute

 Fri, 29 May at 07:00 pm Maryland Hall For The Creative Arts

Annapolis Spring Italian Festa

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

The Psychology of Serial Killers - Annapolis

 Mon, 04 May at 12:00 am Rams Head On Stage - Annapolis

MIGGS | Red Eye’s Dock Bar

 Fri, 29 May at 08:00 pm Red Eye's Dock Bar, Kent Narrows MD

Stephen Lynch

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

Cracker

 Sat, 13 Jun at 07:00 pm Rams Head On Stage

Nao Yoshioka

 Wed, 27 May at 07:00 pm Rams Head On Stage

Annapolis Improv Show - May

 Sat, 09 May at 08:00 pm ArtFarm USD 10

The Super 70's Concert Experience feat. Super Trans Am (Rescheduled from 2/22/26)

 Mon, 18 May Rams Head On Stage - Annapolis

Livingston Taylor at Rams Head On Stage

 Fri, 19 Jun at 08:00 pm Rams Head On Stage

Don Jovi - The Ultimate Tribute to the Music of Bon Jovi

 Fri, 26 Jun at 08:00 pm Rams Head On Stage

Sirens of Spring Tour feat. Mama’s Black Sheep, Sweet Leda Duo, Regina Sayles & Colleen Clark

Thu, 07 May at 08:00 pm Rams Head On Stage

The Marshall Morlock Band

 Wed, 01 Jul at 08:00 pm Rams Head On Stage

Anchors & Artisans @ Annapolis Town Center

 Sun, 17 May at 11:00 am Towne Centre Blvd, Annapolis, MD 21401, United States

Bill Kirchen Band: Cold Light Of Day

 Sun, 17 May at 01:00 pm Rams Head On Stage

Port Annapolis Open House

 Sat, 25 Apr at 10:00 am Safe Harbor Port Annapolis

Lissie

 Thu, 14 May at 07:00 pm Rams Head On Stage

jackrabbit. feat Dermot Mulroney & Kieran Mulroney

 Sat, 30 May at 05:00 pm Rams Head On Stage - Annapolis

Candlelight: Tribute to Fleetwood Mac

 Fri, 29 May at 07:00 pm Maryland Hall For The Creative Arts

Alan Doyle with Bandits on the Run

 Fri, 01 May at 12:00 am Rams Head On Stage - Annapolis

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

Thursday Night LIVE! Featuring Groove Spot Band

 Thu, 18 Jun at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Tommy Prine

 Tue, 09 Jun at 07:00 pm Rams Head On Stage

Bill Kirchen Band

 Sun, 17 May Rams Head On Stage - Annapolis

Thursday Night LIVE! Featuring Honest Lee Soul

 Thu, 16 Jul at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Don Jovi: The Ulimtate Tribute to Bon Jovi

 Sat, 27 Jun at 12:00 am Rams Head On Stage - Annapolis

Adam Hawley in Annapolis

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

Rumours ATL: A Fleetwood Mac Tribute

 Thu, 25 Jun at 08:00 pm Rams Head On Stage

Baltimore's Original Jazz Brunch ft. Ed Hrybyk Trio at The Brass Tap — Ever

 Sun, 26 Apr at 11:00 am The Brass Tap Baltimore Free

Thursday Night LIVE! Featuring Dan Heely

 Thu, 30 Jul at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Revolutionary Annapolis Walking Tour

 Sat, 25 Apr at 11:00 am 99 Main Street, Annapolis, MD, United States, Maryland 21401

Thursday Night LIVE! Featuring Don't Back Down

 Thu, 09 Jul at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Thursday Night LIVE! Featuring Remains of Radio

 Thu, 02 Jul at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Thursday Night LIVE! Featuring The Players Band

 Thu, 27 Aug at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Thursday Night LIVE! Featuring 8 Ohms

 Thu, 06 Aug at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Celtic Cinco de Mayo with La Unica at Rams Head On Stage

 Tue, 05 May at 08:00 pm Rams Head On Stage

Rumours ATL: A Fleetwood Mac Tribute

 Fri, 26 Jun Rams Head On Stage - Annapolis

The Buena Vista Orchestra at Rams Head On Stage

 Sun, 04 Oct at 08:00 pm Rams Head On Stage

BulletBoys Presented by 97Underground.com Radio

 Thu, 06 Aug at 08:00 pm Rams Head On Stage

Southern Culture On The Skids

 Fri, 25 Sep at 07:00 pm Rams Head On Stage

Here Come The Mummies

 Wed, 16 Sep Rams Head On Stage

The Record Company

 Sun, 16 Aug at 07:00 pm Rams Head On Stage

Fink at Rams Head On Stage

 Sun, 02 Aug at 08:00 pm Rams Head On Stage

Adam Hawley

 Thu, 27 Aug Rams Head On Stage

Southern Avenue in Annapolis

 Wed, 12 Aug at 08:00 pm Rams Head On Stage

Mother's Day Dinner

 Sun, 10 May at 05:00 pm Captain's Daughter Free

Dancing Night at Caliente Grill - Class & Social Dance

 Fri, 27 Mar at 07:00 pm Caliente Grill Free

Eastport a rockin Annapolis

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

Put It In The Pock3t "A Night To Remember"

 Sat, 16 May at 06:00 pm Maryland Hall

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

American Voices United Through Song - June 6, 2026

 Sat, 06 Jun at 07:30 pm Maryland Hall USD 0 to 28

Jackrabbit Dermot Mulroney & Kieran Mulroney

 Fri, 29 May at 07:00 pm Rams Head On Stage