Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

Maryland Day Celebration 2026 - filled with fun events!

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

The Sergio Mendes Band at Rams Head On Stage

 Fri, 12 Jun at 09:00 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

Stewart Copeland at Rams Head On Stage

 Tue, 21 Jul Rams Head On Stage

Candlelight: Tribute to Queen & The Beatles

 Fri, 03 Apr at 07:00 pm Maryland Hall For The Creative Arts

Al Di Meola Electric Band

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

Stewart Copeland

 Mon, 20 Jul 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

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

Friends for Friends

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

Thunder From Down Under

 Thu, 26 Mar Rams Head On Stage

Pam Tillis in Annapolis

 Sun, 12 Apr at 07:30 pm Rams Head On Stage

The Lone Bellow at Rams Head On Stage

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

Tommy Castro & The Painkillers

 Mon, 20 Apr at 12:00 am Rams Head On Stage - Annapolis

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

Pam Tillis

 Sat, 11 Apr Rams Head On Stage

Asleep at the Wheel at Rams Head On Stage

 Sat, 16 May 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

Cracker at Rams Head On Stage

 Sun, 14 Jun 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

Shovels & Rope

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

Candlelight: 90s Unplugged

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

Celebrate Maryland Day on Maryland Ave!

 Sat, 21 Mar at 11:00 am 71 Maryland Ave, Annapolis, MD

Jeff Coffin and Rashawn Ross - Apex Jazz and Commercial Music Students at Rams Head On Stage

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

Eddie Money Legacy Band at Rams Head On Stage

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

Duane Betts & Palmetto Motel

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

Milagro Azul: Blue Miracle plays Santana

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

Colin James Matt Anderson & Terra Lightfoot

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

Ally Venable

 Mon, 20 Apr at 08:00 pm Rams Head On Stage

The Annapolis Opry | Paisley, Collins&Vocke, BES, Grasskickers

 Sun, 22 Mar at 02:00 pm St. Margaret's Episcopal Church

Jesse & Dez Money - The Eddie Money Band

 Sat, 18 Apr at 12:00 am Rams Head On Stage - Annapolis

BBMAK with Brian Jarvis

 Thu, 23 Apr at 12:00 am Rams Head On Stage - Annapolis

Annapolis Spring Italian Festa

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

Andrew Duhon

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

Eastport Oyster Boys 30th Anniversary Concert Benefiting Annapolis Musicians For Musicians (AMFM)

 Sun, 22 Mar at 04:00 pm Maryland Hall

Reverend Horton Heat & Black Joe Lewis

 Tue, 07 Apr at 07:00 pm Rams Head On Stage

The Reverend Peyton's Big Damn Band

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

The ASO Family Concert - An Out of This World Music Experience

 Sat, 21 Mar at 11:00 am Maryland Hall for the Creative Arts

The Psychology of Serial Killers - Annapolis

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

AMFM Presents: In The Vane of Eric Clapton

 Mon, 23 Mar at 11:00 pm Rams Head On Stage - Annapolis

Duane Betts at Rams Head On Stage

 Tue, 21 Apr at 08:00 pm Rams Head On Stage

Stephen Lynch

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

Graham Parker

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

Reverend Peyton's Big Damn Band

 Tue, 28 Apr 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

Dancing Night at Caliente Grill - Class & Social Dance

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

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

Carousel of Fun Spring Fling

 Sat, 28 Mar at 10:00 am 89 Bennion Road, 21402

Alan Doyle

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

Big Read of Anne Arundel 2026

 Wed, 01 Apr at 10:00 am Anne Arundel county Maryland

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

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

David Wax Museum

 Sat, 11 Apr Rams Head On Stage - Annapolis

Femmes of Rock

 Thu, 23 Apr at 07:00 pm Rams Head On Stage

Andrew Duhon at Rams Head On Stage

 Tue, 26 May at 08:00 pm Rams Head On Stage

Alan Doyle with Bandits on the Run

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

Cracker

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

Livingston Taylor at Rams Head On Stage

 Fri, 19 Jun Rams Head On Stage

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

 Fri, 10 Apr at 07:00 pm Stan & Joe's Saloon USD 23

Nao Yoshioka

 Wed, 27 May 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

Thursday Night LIVE! Featuring The Players Band

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

7 Bridges: The Ultimate Eagles Experience - Annapolis, MD

 Wed, 26 Aug at 08:00 pm Rams Head On Stage

Burning Witches

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

The Magic of Cinema - April 18, 2026

 Sat, 18 Apr at 07:30 pm Maryland Hall USD 0 to 28

Family Open House at ArtFarm

 Sat, 21 Mar at 12:00 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401

The UN-Gala GALA

 Sat, 18 Apr at 11:00 am Great Frogs Winery USD 290

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

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

Mother's Day Dinner

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

Annapolis Comic-Con

 Fri, 17 Apr at 07:00 pm Byzantium Event and Conference Center

Revolutionary Annapolis Walking Tour

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

An Evening with Jeff Coffin & Rashawn Ross w/ Apex Jazz & Commercial Music Students

 Tue, 14 Apr Rams Head On Stage - Annapolis

Jazz at Lincoln Center PRESENTS: Great American Crooners

 Mon, 13 Apr at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

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

Annapolis Color Run By Color Craze

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

Benjie Porecki

 Sat, 04 Apr at 05:00 pm Rams Head On Stage - Annapolis

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

 Mon, 20 Apr at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Special Guest’s Debut at Ram’s Head Tavern Downbar March 20th

 Fri, 20 Mar at 09:00 pm Rams Head Tavern Annapolis

🎉 St. Margaret’s Church Presents: Galloping for Good 🐎

 Sat, 02 May at 06:00 pm St. Margaret's Church

Nao Yoshioka at Rams Head On Stage

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

Jackrabbit Dermot Mulroney & Kieran Mulroney

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

LIVE MUSIC with Timmie Metz Band

 Fri, 10 Apr at 09:00 pm Blackwall Hitch - Annapolis

Encore Chorale Annapolis Concert

 Thu, 07 May at 07:00 pm Maryland Hall Free

The Talent Machine Co. Presents ~ Broadway Backwards: A Miscast Cabaret!

 Fri, 27 Mar at 07:30 pm Live Arts Maryland Studio USD 30

Pure Comedy: Annapolis Stand Up Showcase

 Sat, 25 Apr at 08:00 pm Pure Boardshop USD 18

Roots Fest: A Maryland Day Kickback celebrating African American History

 Sat, 21 Mar at 05:00 pm The Oaks Inn Annapolis, 172 Green Street, Annapolis, MD 21401

Ridge Grow Grand Opening

Sat, 04 Apr at 10:00 am 244 S Old Mill Bottom Rd, Arnold, MD

10th Annual Spring Sale

 Sat, 11 Apr at 09:00 am 116 Legion Ave., Annapolis, MD, United States, Maryland 21401

Blue Miracle

 Wed, 22 Apr at 07:00 pm Rams Head On Stage

Become a GRIT Architect: Design a Life That Withstands Hard Moments

 Mon, 13 Apr at 06:30 pm 2158 Renard Ct Free

LIVE MUSIC with Michael McHenry Tribe

 Fri, 03 Apr at 09:00 pm Blackwall Hitch - Annapolis

Sirens of Spring at Rams Head On Stage

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

Songbird Festival 2026

 Sun, 03 May at 10:00 am Maryland Hall Free

Burning Witches

 Thu, 02 Apr at 12:00 am Rams Head On Stage - Annapolis

Sweet Leda at Rams Head Roadhouse

 Fri, 03 Apr at 09:00 pm Rams Head Roadhouse

LIVE MUSIC with Rick and The Revolving Doors

 Sat, 25 Apr at 09:00 pm Blackwall Hitch - Annapolis

Shelby Morgan

 Wed, 01 Apr at 07:00 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

Paul Gilbert VIP Experience // Annapolis, MD May 12

 Tue, 12 May at 04:00 pm Rams Head On Stage USD 189 to 269

Spring Afternoon Tea at The Maryland Inn

 Sun, 29 Mar at 11:00 am The Maryland Inn of the Historic Inns of Annapolis USD 15 to 55