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

2026 Annapolis St. Patrick's Hooley!

 Sat, 07 Mar at 05:00 pm U.S. Naval Academy Alumni Association & Foundation USD 178

Stewart Copeland at Rams Head On Stage

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

4th Annual Peake Irish Experience for Annapolis St Patrick's Day on 3/7

 Sat, 07 Mar at 12:00 pm Main Street USD 7 to 29

Black Violin: Full Circle at Rams Head On Stage

 Sat, 28 Feb at 03:00 pm Rams Head On Stage

Colin James, Matt Andersen, Terra Lightfoot in Annapolis

 Wed, 06 May at 08:00 pm Rams Head On Stage

John Moreland and Patterson Hood

 Sun, 15 Mar at 11:00 pm Rams Head On Stage - Annapolis

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 Official Annapolis Shamrock Stroll

 Sat, 07 Mar at 12:00 pm The Best Bars in Annapolis USD 5

Al Di Meola Electric Band

 Fri, 08 May 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

Friends for Friends

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

Krewe of the Clawdagh -Annapolis St Patrick's Day Parade

 Sun, 08 Mar at 01:00 pm Annapolis, Maryland

Candlelight: Tribute to Queen & The Beatles

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

Pam Tillis in Annapolis

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

Pam Tillis

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

Alan Doyle, Bandits on the Run in Annapolis

 Thu, 30 Apr at 08:00 pm Rams Head On Stage

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

Tommy Castro & The Painkillers

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

Annapolis First Sunday Arts Festival

Sun, 03 May at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Candlelight: 90s Unplugged

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

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

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

 Tue, 14 Apr Rams Head On Stage

Eddie Money Legacy Band at Rams Head On Stage

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

Sue Foley

 Thu, 12 Mar at 07:00 pm Rams Head On Stage

The High Kings

 Sun, 08 Mar at 09:00 pm Rams Head On Stage - Annapolis

SAT 3/7/26: Third Eye Faithful Day 2026 - The Next Chapter

 Sat, 07 Mar at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Alan Doyle

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

Celebrate Maryland Day on Maryland Ave!

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

Reverend Horton Heat & Black Joe Lewis

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

Duane Betts & Palmetto Motel

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

Duane Betts at Rams Head On Stage

 Tue, 21 Apr 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

Femmes of Rock

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

Reverend Peyton's Big Damn Band

 Tue, 28 Apr at 07:00 pm Rams Head On Stage

Graham Parker

 Fri, 01 May Rams Head On Stage

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

 Fri, 06 Mar at 07:00 pm Stan & Joe's Saloon USD 23

David Wax Museum

 Sat, 11 Apr at 12:00 am Rams Head On Stage - Annapolis

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

Burning Witches

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

Stephen Lynch

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

Cracker

 Sat, 13 Jun Rams Head On Stage

The Reverend Peyton's Big Damn Band

 Thu, 30 Apr Rams Head On Stage - Annapolis

The Psychology of Serial Killers - Annapolis

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

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

Annapolis Spring Improv Show

 Sat, 14 Mar at 07:00 pm ArtFarm USD 10

The UN-Gala GALA

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

St. Patrick's Day Parade Ride

 Sun, 08 Mar at 12:45 pm Annapolis, MD

The Magic of Cinema - April 18, 2026

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

Uli Jon Roth

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

Zumba with Diana Bobrow

 Thu, 19 Mar at 06:30 pm 2158 Renard Ct Free

Annapolis Comic-Con

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

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

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

LIVE MUSIC: Suzy & Shawn in downbar

 Sat, 28 Feb at 09:00 pm Rams Head Tavern Annapolis

Live Music with The Loose Ends

 Sat, 28 Feb at 09:00 pm Rams Head Roadhouse

Jazz at Lincoln Center PRESENTS: Great American Crooners

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

An Evening with Branford Marsalis

 Sun, 01 Mar at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

Taj Farrant

 Tue, 17 Mar at 07:00 pm Rams Head On Stage

American Voices United Through Song - June 6, 2026

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

Green River: 15th Anniversary Legacy Tour

 Sat, 07 Mar at 08:00 pm Rams Head On Stage

Signature Series: Echoes of Heritage with Olga Kern, piano

 Sat, 28 Feb at 07:30 pm Maryland Hall for the Creative Arts

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

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

Pure Comedy: Annapolis Stand Up Showcase

 Sat, 14 Mar at 08:00 pm Pure Boardshop USD 18

NEW DATE - WED 3/11/26: Punisher #1 Launch Signing with Writer Ben Percy

 Wed, 11 Mar at 07:00 pm 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Annapolis Spring Italian Festa

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

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

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

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

The First Class – Free Film Screening | NVA Annapolis

 Mon, 02 Mar at 05:45 pm 1410 West St, Annapolis, MD 21401-4036, United States

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

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

Parking The Phil Collins Experience

 Wed, 18 Mar at 12:00 am Rams Head On Stage - Annapolis

Ridge Grow Grand Opening

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

Fuerza y Energía: Movimiento para Tu Cuerpo y Tu Vida

 Thu, 07 May at 06:30 pm 2158 Renard Ct Free

LIVE MUSIC with ONO Band

 Sat, 28 Feb at 09:00 pm Blackwall Hitch - Annapolis

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

Songbird Festival 2026

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

Pure Comedy: Annapolis Stand Up Showcase

 Fri, 13 Mar at 08:00 pm Pure Boardshop USD 18

A Women’s Wellness Dance Party

 Fri, 29 May at 07:00 pm 2158 Renard Ct Free

Paul Gilbert VIP Experience // Annapolis, MD May 12

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

A Tale of Two Cities

 Wed, 25 Feb at 07:00 pm Main Stage At Classic Theatre of Maryland

Thunder from Down Under

 Thu, 26 Mar at 07:00 pm Rams Head On Stage

LIVE MUSIC with Timmie Metz Band

 Fri, 27 Feb at 09:00 pm Blackwall Hitch - Annapolis

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

Pierce Pettis with Special Guest Danielle Howle in Annapolis

 Mon, 17 Aug at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Burning Witches

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

Hazy Dayz Beer Release Party!

 Thu, 05 Mar at 04:00 pm Rams Head Roadhouse

The Good Deale Bluegrass & Eastman String Band

 Sun, 22 Mar at 12:00 am Rams Head On Stage - Annapolis

Sirens of Spring at Rams Head On Stage

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

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

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

All-Ages Barn Dance - FREE!

 Sun, 22 Mar at 03:00 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401

Jeffrey Gaines, Sawyer Fredericks in Annapolis

 Sun, 01 Mar at 07:00 pm Rams Head On Stage

John Moreland at Rams Head On Stage

 Sun, 15 Mar at 07:00 pm Rams Head On Stage

One Step Down at Rams Head Tavern in Annapolis, MD

 Thu, 21 May at 05:00 pm Rams Head Tavern Annapolis

PMI-ACP® Classroom Agile Certification Course in Annapolis, MD

 Wed, 11 Feb at 09:00 am 1910 Towne Centre Blvd USD 1,599

Versed Fox Book Club

 Wed, 10 Jun at 07:00 pm 35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

Rams Head Roadhouse

Sat, 07 Mar at 08:00 pm Ramshead Roadhouse

Holy Matribunny: Celebrate The Wedding of Hotsy & Totsy!

 Sat, 28 Feb at 05:30 pm Paws at the Mall USD 29

Wellness With a Little Drama

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