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

Black Violin: Full Circle at Rams Head On Stage

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

Black Violin

 Fri, 27 Feb at 07:00 pm Rams Head On Stage

2026 Annapolis St. Patrick's Hooley!

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

Emmaline: LIVE in Annapolis, MD "Be My Valentine" Tour

Sun, 15 Feb 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

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

Comics for Critters

 Mon, 09 Feb at 07:00 pm Federal House Bar & Grille USD 23 to 215

Tommy Castro & The Painkillers

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

Billy Price Band

 Sat, 31 Jan at 07:00 pm Rams Head On Stage

Sue Foley

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

Dan Tyminski Band

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

Naptown Brass Band Mardi Gras at Rams Head!!!

 Tue, 17 Feb at 08:00 pm Rams Head On Stage

The Super 70's Concert Experience feat. Super Trans Am at Rams Head On Stage

 Sun, 22 Feb at 08:00 pm Rams Head On Stage

The High Kings

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

Capitol Fools

 Fri, 06 Feb at 07:00 pm Rams Head On Stage

Reverend Horton Heat & Black Joe Lewis

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

Chesapeake Winter Bluegrass FESTIVAL

 Fri, 30 Jan at 12:00 pm Crowne Plaza Annapolis

Chuck Brown Band

 Sun, 01 Feb at 01:30 am Rams Head On Stage - Annapolis

AMFM Presents: A Tribute to Grateful Dead & Bob Weir

Mon, 16 Feb at 06:30 pm Rams Head On Stage

Femmes of Rock

 Thu, 23 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

Dio Rules: A Tribute to Rainbow, Black Sabbath & Dio

Thu, 19 Feb at 08:00 pm Rams Head On Stage

Signature Series: "Legends" with soprano Christine Goerke at Maryland Hall

 Sat, 31 Jan at 07:30 pm Maryland Hall for the Creative Arts

Signature Series: "Legends" with soprano Christine Goerke at Maryland Hall

 Fri, 30 Jan at 07:30 pm Maryland Hall for the Creative Arts

Maryland Tourism Day 2026

Fri, 13 Feb at 08:30 am Rams Head On Stage

Quinn Sullivan at Rams Head On Stage

 Sat, 21 Mar Rams Head On Stage

🎸The Linda Ronstadt Experience w/American Idol Star Tristan McIntosh Returns to Rams Head

Thu, 26 Feb at 07:30 pm Rams Head Tavern Annapolis

Stephen Lynch

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

Legends & Landcapes - February 22, 2026

 Sun, 22 Feb at 03:00 pm Maryland Hall USD 0 to 28

The Honey Dew Drops in Annapolis, MD.

 Mon, 16 Feb at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 20

The Young Fables in Annapolis, MD

 Fri, 20 Feb at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

The Psychology of Serial Killers - Annapolis

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

Burning Witches

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

Suede

 Thu, 19 Feb at 07:00 pm Rams Head On Stage

Taj Farrant

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

LIVE MUSIC with Bravenoise

 Fri, 30 Jan at 09:00 pm Blackwall Hitch - Annapolis

WED 2/25/26: Punisher #1 Launch Signing with Writer Ben Percy

 Wed, 25 Feb at 07:00 pm 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

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

 Fri, 20 Feb at 07:00 pm Stan & Joe's Saloon USD 23

LIVE MUSIC with Alt Rewind

 Sat, 14 Feb at 09:00 pm Blackwall Hitch - Annapolis

LIVE MUSIC with Michael McHenry Tribe

 Fri, 06 Feb at 09:00 pm Blackwall Hitch - Annapolis

The Magic of Cinema - April 18, 2026

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

Masquerade Party

 Tue, 17 Feb at 07:00 pm Captain's Daughter Free

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

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

Brandon Hardesty of Bumpin' Uglies w/ Nate Finn

 Thu, 12 Feb at 08:00 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

Annapolis First Sunday Arts Festival

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

Beige Atelier Galentines Tox Party Event

 Sat, 07 Feb at 12:00 pm Beige Atelier Regenerative & Aesthetic Medicine Free

Honky Tonk Casanovas Comes to The Annapolis Smokehouse

 Sat, 21 Feb at 08:30 pm Annapolis Smokehouse and Tavern

Parking The Phil Collins Experience

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

Fallin Free - A Tribute to Tom Petty and The Heartbreakers

 Fri, 20 Feb at 07:00 pm Rams Head On Stage

Annapolis Contra Dance! Chloe Levine calls with The Jay Birds!

 Sat, 31 Jan at 06:30 pm Annapolis Friends Meeting, Quakers

Signature Series: Echoes of Heritage with Olga Kern, piano

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

Jeffrey Gaines, Sawyer Fredericks in Annapolis

 Sun, 01 Mar 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

Music Trivia - Cape Vibes Fundraiser!!

 Fri, 27 Feb at 06:00 pm Cape St. Claire Improvement Association

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

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

Green River: 15th Anniversary Legacy Tour

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

Dan Haas - reHAASh reTROSPECTIve

 Sat, 07 Feb 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

Navy Midshipmen Lacrosse vs. High Point Panthers

 Fri, 30 Jan Navy Marine Corps Memorial Stadium

Lonesome River Band at Chesapeake Winter Bluegrass

 Sat, 31 Jan at 03:00 pm Crowne Plaza Annapolis

Songbird Festival 2026

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

LIVE MUSIC with ONO Band

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

LIVE MUSIC with Timmie Metz Band

 Fri, 13 Feb at 09:00 pm Blackwall Hitch - Annapolis

A Women’s Wellness Dance Party

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

LIVE MUSIC with Bravenoise

 Fri, 20 Feb at 09:00 pm Blackwall Hitch - Annapolis

Know Return at Rams Head On Stage

 Sun, 29 Mar at 08:00 pm Rams Head On Stage

The Official Annapolis Shamrock Stroll

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

LIVE MUSIC with Timmie Metz Band

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

Sweet Leda at Rams Head Roadhouse

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

Zumba with Diana Bobrow

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

Burning Witches

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

Glow in the dark Paint Party

 Thu, 19 Feb at 06:00 pm Greenbury Point

The Good Deale Bluegrass & Eastman String Band

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

Cyphers Band @ Annapolis Smokehouse 2/6/26 🔥 Free show!

 Fri, 06 Feb at 08:30 pm Annapolis Smokehouse and Tavern

Thunder from Down Under

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

Live on the Red Stage at ArtFarm!

 Sat, 21 Feb at 06:00 pm ArtFarm USD 29

With Quill and Voice: A Valentine of Verse and Song from the Literary Salons of 17th-Century England

 Sat, 14 Feb at 06:00 pm 19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

Cherish the Ladies

 Mon, 02 Mar at 07:00 pm Rams Head On Stage

Mardi Gras @ Forward Brewing

 Tue, 17 Feb at 07:00 pm 926 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403

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

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

Wellness With a Little Drama

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

Rams Head Roadhouse

Sat, 07 Mar at 08:00 pm Ramshead Roadhouse

Rams Head Roadhouse

Sat, 06 Jun at 08:00 pm Ramshead Roadhouse

Annapolis' Secret Society: Mystery Hunt

 Sat, 26 Jul at 05:00 pm 43 Calvert St USD 10 to 20

Fuerza y Energía: Movimiento para Tu Cuerpo y Tu Vida

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

Annapolis Darkverse Color Run

 Sat, 23 May at 06:00 pm Annapolis, Annapolis, Maryland

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

 Mon, 13 Apr at 06:30 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

Annapolis Comic-Con

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

Annapolis M**der Mystery: Catch the Killer!

 Sat, 31 May at 11:00 am 101 State Cir USD 10 to 20

Jonathan Sloane in Annapolis, MD

 Mon, 15 Jun at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Naptown Brass Band

 Mon, 16 Feb at 07:00 pm Rams Head On Stage

BoDeans

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

Hollywood Nights

 Thu, 26 Mar at 08:00 pm Rams Head On Stage

A Tale of Two Cities

 Tue, 24 Feb at 07:00 pm Main Stage At Classic Theatre of Maryland

Parking Albert Lee

 Tue, 17 Mar at 12:00 am Rams Head On Stage - Annapolis

Uli Jon Roth

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