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

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

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

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

Pam Tillis

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

The Smithereens in Annapolis

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

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

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

Candlelight: A Haunted Evening of Halloween Classics

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

The Smithereens

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

Candlelight: Coldplay & Imagine Dragons

 Sat, 30 May at 04:30 pm Maryland Hall USD 31 to 79

Candlelight: Tribute to Fleetwood Mac

 Sat, 30 May at 06:45 pm Maryland Hall USD 47 to 89

Robyn Hitchcock at Rams Head On Stage

 Wed, 17 Jun at 08:00 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

Candlelight: 90s Unplugged

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

The Smithereens w. Guest Vocalist Marshall Crenshaw

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

Annapolis First Sunday Arts Festival

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

Los Lonely Boys at Rams Head On Stage

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

Acoustic Brunch Sail with Gareth Asher

 Mon, 25 May at 10:30 am 80 Compromise Street, Annapolis, MD, United States, Maryland 21401

Shovels & Rope in Annapolis

 Fri, 10 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

Andrew Duhon

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

Andrew Duhon at Rams Head On Stage

 Tue, 26 May Rams Head On Stage

Paca Girlfriends Party - A Fundraiser to Benefit Historic Annapolis

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

The Sergio Mendes Band

 Thu, 11 Jun 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

Stephen Lynch

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

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

 Mon, 18 May at 12:00 am Rams Head On Stage - Annapolis

Bill Kirchen Band

 Sun, 17 May Rams Head On Stage - Annapolis

Cracker at Rams Head On Stage

 Sun, 14 Jun Rams Head On Stage

Marion Meadows, Alex Bugnon in Annapolis

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

Nao Yoshioka

 Wed, 27 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

Michael Cleveland in Annapolis

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

Freddy Jones Band w. Chris Stake

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

Augustana

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

East Nash Grass at Rams Head On Stage

 Sun, 12 Jul Rams Head On Stage

Rumours ATL: A Fleetwood Mac Tribute

 Fri, 26 Jun Rams Head On Stage - Annapolis

Candlelight: Tribute to Fleetwood Mac

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

Thursday Night LIVE! Featuring The Chucks

 Thu, 11 Jun 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

Thursday Night LIVE! Featuring Sweet Leda

 Thu, 04 Jun at 06:30 pm 307 Sail Pl, Annapolis, MD 21401, United States

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

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

Fink at Rams Head On Stage

 Sun, 02 Aug Rams Head On Stage

The Record Company

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

MIGGS | Red Eye’s Dock Bar

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

Southern Culture On The Skids

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

The Annapolis Arts Week ART PARTY!

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

Tommy Prine

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

Die Laughing Presents: "Hit Me 90s One More Time" - Comedy Murder Mystery

 Thu, 21 May 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

Thursday Night LIVE! Featuring Honest Lee Soul

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

Bridges : The Ultimate EAGLES Experience

 Thu, 27 Aug Rams Head On Stage - Annapolis

The Marshall Morlock Band

 Wed, 01 Jul 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

Bill Kirchen Band: Cold Light Of Day

 Sun, 17 May at 01:00 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

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

 Thu, 28 May at 08:00 pm TGI Fridays Free

Dancing Night at Caliente Grill - Class & Social Dance

 Fri, 22 May at 07:00 pm Caliente Grill USD 7 to 13

Paul Cullen - Good Times with Bad Company

 Fri, 22 May at 07:30 pm Annapolis Mall USD 0 to 34

Dancing Night at Caliente Grill - Class & Social Dance

 Fri, 27 Mar at 07:00 pm Caliente Grill USD 5 to 10

Here Come The Mummies

 Wed, 16 Sep Rams Head On Stage

Adam Hawley

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

Thursday Night LIVE! Featuring Dan Heely

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

American Voices United Through Song - June 6, 2026

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

BulletBoys Presented by 97Underground.com Radio

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

Cracker

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

Thursday Night LIVE! Featuring 8 Ohms

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

Livingston Taylor at Rams Head On Stage

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

Thursday Night LIVE! Featuring The Players Band

 Thu, 27 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

Eastport a rockin Annapolis

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

Thursday Night LIVE! Featuring Remains of Radio

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

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

Jackrabbit Dermot Mulroney & Kieran Mulroney

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

Nao Yoshioka at Rams Head On Stage

 Thu, 28 May at 08:00 pm Rams Head On Stage

Southern Avenue in Annapolis

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

Live Arts Maryland Musical Theater Summer Intensive

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

Bountiful Harvest - Costumes & Cocktails

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

East Nash Grass

 Sat, 11 Jul at 07:00 pm Rams Head On Stage

Blank Page & Chris Diller

 Sun, 02 Aug Rams Head On Stage

Mermaid Storytime & Wish Ceremony

 Sat, 30 May at 03:00 pm Annapolis Friends Meeting USD 0 to 61

Delegate Bagnall @ Cape St. Claire Strawberry Festival!

 Sat, 06 Jun at 10:00 am Cape St. Claire Improvement Association

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

SYT Skate Session

 Sat, 06 Jun at 02:00 pm 300 Truxtun Park Rd Free

Indigenous

 Fri, 22 May Rams Head On Stage

Thursday Night LIVE! Featuring Don't Back Down

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

Annapolis Color Run By Color Craze

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

In her own voice: celebrating women in jazz

 Sun, 24 May at 07:00 pm 49 West Coffeehouse, Winebar & Gallery

Adam Hawley in Annapolis

 Fri, 28 Aug at 08:00 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

Royale Lynn at Rams Head On Stage

 Thu, 16 Jul at 08:00 pm Rams Head On Stage

Colonial Garden Party

 Sun, 17 May at 12:00 pm 186 Prince George St, Annapolis, MD 21401-1724, United States

Wellness With a Little Drama

 Thu, 04 Jun at 06:30 pm 2158 Renard Ct Free