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

Eastport a Rockin' 2026

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

Stewart Copeland at Rams Head On Stage

 Tue, 21 Jul Rams Head On Stage

Stewart Copeland

 Mon, 20 Jul at 07:00 pm 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

PJ Morton

 Mon, 03 Aug at 07:00 pm Rams Head On Stage

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

Nitro Circus 2.0 – Annapolis, MD

 Sun, 23 Aug at 06:00 pm 550 Taylor Ave, Annapolis, MD 21401, United States

Sérgio Mendes in Annapolis

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

Robyn Hitchcock at Rams Head On Stage

 Wed, 17 Jun at 08:00 pm Rams Head On Stage

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

The Sergio Mendes Band

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

Digable Planets: Celebrating 30 years of Blow Out Comb

 Wed, 05 Aug at 08:00 pm Maryland Hall

Cracker at Rams Head On Stage

 Sun, 14 Jun Rams Head On Stage

Los Lonely Boys at Rams Head On Stage

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

Candlelight: A Haunted Evening of Halloween Classics

 Thu, 29 Oct at 08:45 pm Maryland Hall USD 31 to 76

Shovels & Rope in Annapolis

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

Pam Tillis

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

Candlelight: 90s Unplugged

 Sat, 18 Jul at 06:45 pm Maryland Hall USD 31 to 76

The Robert Cray Band in Annapolis

 Wed, 16 Sep at 08:00 pm Rams Head On Stage

Ari Hest at 49 West in Annapolis, MD

 Mon, 16 Nov at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Josh Blue at Rams Head On Stage

 Thu, 15 Oct at 08:00 pm Rams Head On Stage

Hell's Belles

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

Marion Meadows, Alex Bugnon in Annapolis

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

Who's Bad - Michael Jackson Tribute Band

 Sat, 18 Jul Rams Head On Stage

Paca Girlfriends Party - A Fundraiser to Benefit Historic Annapolis

 Wed, 10 Jun at 06:00 pm Paca House and Garden

Tab Benoit w/ Sgt. Splendor

Tue, 14 Jul at 08:00 pm Rams Head On Stage

AcoustiCafe Returns to Goshen Farm

 Fri, 10 Jul at 06:30 pm Historic Goshen Farm & Educational Center

Annapolis First Sunday Arts Festival

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

Augustana // ATSAB 20th Anniversary (Solo): An Intimate Performance of the Album in Full

 Fri, 17 Jul at 08:00 pm Rams Head On Stage

Candlelight: Coldplay & Imagine Dragons

 Sat, 18 Jul at 04:30 pm Maryland Hall USD 31 to 73

Mike Phillips

 Sun, 30 Aug at 08:00 pm Rams Head On Stage

Livingston Taylor at Rams Head On Stage

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

East Nash Grass at Rams Head On Stage

 Sun, 12 Jul Rams Head On Stage

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

Rumours ATL: A Fleetwood Mac Tribute

 Fri, 26 Jun Rams Head On Stage - Annapolis

Don Jovi: The Ulimtate Tribute to Bon Jovi

 Sat, 27 Jun Rams Head On Stage - Annapolis

Fink at Rams Head On Stage

 Sun, 02 Aug Rams Head On Stage

Krimson Tide: The Kritical Yacht Party of the Summer

 Sat, 18 Jul at 06:00 pm 1 Dock St USD 95 to 189

The Record Company

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

Freddy Jones Band w. Chris Stake

 Sat, 25 Jul at 08:00 pm Rams Head On Stage

Adam Hawley

 Thu, 27 Aug at 07:00 pm Rams Head On Stage

The Buena Vista Orchestra at Rams Head On Stage

 Sun, 04 Oct 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

Sean Hayes at Rams Head On Stage

 Wed, 23 Sep at 08:00 pm Rams Head On Stage

Thursday Night LIVE! Featuring Honest Lee Soul

 Thu, 16 Jul 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

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

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

Thursday Night LIVE! Featuring Groove Spot Band

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

Bridges : The Ultimate EAGLES Experience

 Thu, 27 Aug at 12:00 am Rams Head On Stage - Annapolis

Hudson River Line: The Music of Billy Joel

Sat, 04 Jul at 02:00 pm Rams Head On Stage

Augustana

 Thu, 16 Jul at 07:00 pm Rams Head On Stage

Donavon Frankenreiter: Ask Me Anything Tour w/ Iris And The Shade

 Thu, 20 Aug at 08:00 pm Rams Head On Stage

Thursday Night LIVE! Featuring Unity Reggae Band

 Thu, 25 Jun at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

Thursday Night LIVE! Featuring Don't Back Down

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

Laughs in the Lounge

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

Southern Avenue in Annapolis

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

Thursday Night LIVE! Featuring Remains of Radio

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

Adam Hawley in Annapolis

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

Legacy Five in Annapolis

 Sat, 20 Jun at 06:00 pm Weems Creek Baptist Church

The Annapolis Arts Week ART PARTY!

 Fri, 12 Jun at 06:00 pm AND Creative Studio USD 29

We Are the Queerdos, Mister: A Burlesque Tribute to Queer Icons

 Sat, 13 Jun at 07:00 pm ArtFarm USD 25

Bullet Boys

 Fri, 07 Aug at 12:00 am Rams Head On Stage - Annapolis

Thursday Night LIVE! Featuring 8 Ohms

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

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

Thursday Night LIVE! Featuring The Players Band

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

Rumours ATL: A Fleetwood Mac Tribute

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

Cracker

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

Eastport a rockin Annapolis

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

Thursday Night LIVE! Featuring Dan Heely

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

BulletBoys Presented by 97Underground.com Radio

 Thu, 06 Aug 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

Naptown Cruise

 Fri, 19 Jun at 08:00 pm 1 Dock St, Annapolis, MD 21401

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

Technicolor Motor Home: A Tribute to Steely Dan

 Sat, 10 Oct at 08:00 pm Rams Head On Stage

Parker Barrow

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

Cracker

 Mon, 15 Jun at 12:00 am Rams Head On Stage - Annapolis

Ghalia Volt w. Kent Burnside

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

East Nash Grass

 Sat, 11 Jul Rams Head On Stage

Blank Page & Chris Diller

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

Acoustic Alchemy

 Tue, 20 Oct at 08:00 pm Rams Head On Stage

LA Guns VIP // June 07 Annapolis, MD

 Sun, 07 Jun at 05:30 pm Rams Head On Stage USD 135

Fink

 Sat, 01 Aug at 07:00 pm Rams Head On Stage

LIVE AT THE FILLMORE: The Midterm Tour!

Sat, 22 Aug at 08:00 pm Rams Head On Stage

Bountiful Harvest - Costumes & Cocktails

 Fri, 23 Oct at 07:00 pm 10 Hudson St, Annapolis, MD, United States, Maryland 21401

The Marshall Morlock Band at Rams Head On Stage

 Wed, 01 Jul Rams Head On Stage

Southern Avenue

 Thu, 13 Aug at 12:00 am Rams Head On Stage - Annapolis

Live Arts Maryland Musical Theater Summer Intensive

 Mon, 22 Jun at 10:00 am Annapolis Mall USD 482

June Improv Comedy Show

 Sat, 20 Jun at 08:00 pm ArtFarm USD 10

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

The Best of Broadway

 Sun, 14 Jun at 07:00 pm Cabaret Room at Classic Theatre of Maryland

The Marshall Morlock Band

 Thu, 02 Jul Rams Head On Stage - Annapolis

Tots@10:00 - Beach Party

 Tue, 21 Jul at 10:00 am 307 Sail Pl, Annapolis, MD 21401, United States

Maryland Hall Presents: Classical Music for People with Short Attention Spans

 Sat, 27 Jun at 11:00 am 801 Chase St, Annapolis, MD, United States, Maryland 21401

Herman's Hermits & Peter Noone

 Sat, 21 Nov Rams Head On Stage USD 71 to 88

Amy Speace in Annapolis, MD

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