Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

New Year's Eve Annapolis Yacht Party

 Wed, 31 Dec at 08:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

The Choptank's New Years Eve Party

 Wed, 31 Dec at 08:00 pm The Choptank - Annapolis USD 143 to 228

New Year's Eve at Acqua al 2

 Wed, 31 Dec at 08:45 pm Acqua al 2 - Annapolis, Main Street, Annapolis, MD, USA USD 150

A Very Merry Drag Brunch

Sun, 21 Dec at 12:30 pm Rams Head On Stage

Last Train Home

 Fri, 02 Jan at 08:00 pm Rams Head On Stage

Pressing Strings

 Sun, 28 Dec at 08:00 pm Rams Head On Stage

Siren's Call

 Fri, 26 Dec at 05:00 pm The Westin Annapolis Free

2026 Annapolis St. Patrick's Hooley!

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

A Fright Before Christmas - Ghost Story Dinner at Middleton Tavern

 Tue, 23 Dec at 06:30 pm Middleton Tavern

Scorpion Rose

Sat, 20 Dec at 09:00 pm Blackwall Hitch - Annapolis

Women's Christmas Party

 Sat, 20 Dec at 10:00 am Crowne Plaza Annapolis, an IHG Hotel Free

Eric Scott's Annual Holiday Celebration with very Special Guest Tony Denikos

 Mon, 15 Dec at 07:30 pm 49 West Coffeehouse, Winebar & Gallery

Jimmie's Chicken Shack Holidaze Show

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

Tides & Tunes

 Tue, 16 Dec at 05:00 pm The Westin Annapolis Free

Holiday Pops at Maryland Hall

 Fri, 19 Dec at 07:30 pm Maryland Hall for the Creative Arts

Danny Burns Band: Southern Sky Album Release Tour

 Mon, 22 Dec at 08:00 pm Rams Head On Stage

Military Bowl

 Fri, 26 Dec Navy Marine Corps Memorial Stadium

Tides & Tunes

 Tue, 23 Dec at 05:00 pm The Westin Annapolis Free

Danny Burns Band

 Sun, 21 Dec at 07:00 pm Rams Head On Stage

The Chuck Brown Band (Dance Area!)

Sat, 31 Jan at 08:30 pm Rams Head On Stage

January Film Club - "Passion of Joan of Arc" (1928) w/ live music accomp

 Fri, 23 Jan at 06:00 pm AND Creative Studio USD 18

Songs of the Season - a holiday concert and sing-along

 Sun, 14 Dec at 03:00 pm Eastport United Methodist Church USD 0 to 12

Jarrod Lawson concert at Rams Head On Stage

 Sat, 17 Jan at 08:00 pm Rams Head On Stage

The Honey Dew Drops in Annapolis, MD.

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

December Film Club - "The Exterminating Angel" (1962)

 Fri, 19 Dec at 06:00 pm AND Creative Studio USD 18

AMFM & Songbird Collective Present: A Tribute to Aretha Franklin (matinee)

Sun, 25 Jan at 12:30 pm Rams Head On Stage

Kashmir - The Led Zeppelin Experience

 Fri, 09 Jan at 07:00 pm Rams Head On Stage

Rams Head Presents The Bacon Brothers: Freestanding Tour - Maryland Hall - Annapolis, MD

 Thu, 22 Jan at 08:00 pm Maryland Hall

Dave Matthews Tribute Band

 Sat, 24 Jan at 07:00 pm Rams Head On Stage

Jon McLaughlin & Friends: Home For The Holidays with T.3

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

T Rose International Bridal Show Annapolis January 2026

 Sun, 04 Jan at 12:00 pm Crowne Plaza Annapolis, an IHG Hotel USD 18

The Young Fables in Annapolis, MD

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

Ana Popovic: Dance To The Rhythm Tour (Matinee)

Sun, 11 Jan at 01:00 pm Rams Head On Stage

Danah Denice Band at Rams Head On Stage

 Fri, 16 Jan at 08:00 pm Rams Head On Stage

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

Sun, 15 Feb at 08:00 pm Rams Head On Stage

Fireside Revelry: A Colonial Twelfth Night Concert

 Sat, 10 Jan at 06:00 pm 19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

LIVE MUSIC with Rick & The Revolving Doors

 Sat, 13 Dec at 09:00 pm Blackwall Hitch - Annapolis

Live Arts Maryland Presents Handel's Messiah

 Sun, 21 Dec at 03:00 pm St. Anne's Parish USD 0 to 39

Annapolis Darkverse Color Run

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

Dead Letter Office: A Tribute of R.E.M

 Sun, 11 Jan at 08:00 pm Rams Head On Stage

A SQRRL! Holiday at Rams Head On Stage

 Sat, 20 Dec at 12:00 pm Rams Head On Stage

Ram's Head on Stage

 Sat, 10 Jan at 08:30 pm Rams Head On Stage

LIVE MUSIC with Moon Cherry

 Fri, 19 Dec at 09:00 pm Blackwall Hitch - Annapolis

LIVE MUSIC with Timmie Metz Band

 Fri, 26 Dec at 09:00 pm Blackwall Hitch - Annapolis

Bill Starks with Greg Hardin in Annapolis

 Tue, 20 Jan at 07:30 pm 49 West Coffeehouse, Winebar & Gallery USD 23

Candlelight: Christmas Carols on Strings | Annapolis

 Sun, 21 Dec at 04:30 pm Annapolis Waterfront Hotel

LIVE MUSIC with Enslow

 Fri, 26 Dec at 09:00 pm Blackwall Hitch - Annapolis

Paint Night @ NEO PIZZA - Annapolis

 Wed, 17 Dec at 06:00 pm Neo Pizza & Taphouse USD 40

Carbon Leaf: 'I Want To Be Leaf' Tour 2025

 Sun, 14 Dec at 01:00 pm Rams Head On Stage

Cash Unchained – The Ultimate Johnny Cash Tribute

 Thu, 22 Jan at 08:00 pm Rams Head On Stage

DMTB: The Dave Matthews Tribute Band: Tomorrow We Die Tour

 Sun, 25 Jan at 08:00 pm Rams Head On Stage

Legends & Landcapes - February 22, 2026

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

Noelle & Jeff Full Band!

 Fri, 02 Jan at 10:00 pm Middleton Tavern

Tell Me Lies - The Fleetwood Mac Experience

 Thu, 08 Jan at 08:00 pm Rams Head On Stage

Bruce in the USA: The World's #1 Tribute to Bruce Springsteen and the E Street Band

 Fri, 23 Jan at 08:00 pm Rams Head On Stage

Crushed Glass Ornaments @ NEO Pizza w/MD Craft Parties

 Tue, 16 Dec at 06:00 pm Neo Pizza Annapolis USD 55

PARKING: Military Bowl

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

Danah Denice Band

 Thu, 15 Jan at 07:00 pm Rams Head On Stage

Shakey Graves, Clover County in Annapolis

 Sun, 14 Dec at 08:00 pm Rams Head On Stage

Ave Maria A Christmas Concert

 Sun, 14 Dec at 04:00 pm 1120 Spa Road, Annapolis, MD, United States, Maryland 21403

LIVE MUSIC with Aiden Ewald

 Thu, 18 Dec at 06:00 pm Blackwall Hitch - Annapolis

SQRRL! HOLIDAY! Kids Musical Extravaganza! MATINEE SHOW w/ The Christmas Wish Crackler!

 Sat, 20 Dec at 12:00 pm Rams Head On Stage

Suede

 Thu, 19 Feb Rams Head On Stage

The Seldom Scene

 Mon, 29 Dec at 07:00 pm Rams Head On Stage

Tides & Tunes

 Tue, 30 Dec at 05:00 pm The Westin Annapolis Free

The Magic of Cinema - April 18, 2026

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

American Voices United Through Song - June 6, 2026

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

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

 Wed, 14 Jan at 08:00 pm Rams Head On Stage

Fallin' Free: A Tribute to Tom Petty & The Heartbreakers feat. Scott Kurt

 Sat, 21 Feb at 08:00 pm Rams Head On Stage

Captain Mike & The Shipwrecked

 Thu, 29 Jan at 08:00 pm Rams Head On Stage

2026 Mountain Maryland PACE

 Thu, 22 Jan at 05:00 pm The Westin Annapolis USD 189 to 242

Holiday Ceramic Lantern Party @ NEO Pizza Annapolis /Maryland Craft Parties

 Tue, 16 Dec at 06:00 pm Neo Pizza Annapolis USD 47

The Dave Matthews Tribute Band

 Sat, 24 Jan at 07:00 pm Rams Head On Stage

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

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

The High Kings in Annapolis

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

Jonathan Butler in Annapolis

 Sat, 18 Apr at 06:30 pm Rams Head On Stage

Bay Winds Band Holiday Winter Concert "Set the Scene" with Holiday Fun!

 Tue, 16 Dec at 07:30 pm Unity by the Bay (Maryland)

Sons of Cream feat. Kofi Baker & Malcolm Bruce w/ special guest Rob Johnson

 Fri, 27 Feb at 08:00 pm Rams Head On Stage

Billy Price Band

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

The New Romance: The Ultimate 80s Prom NYE Dance Party at Rams Head On Stage

 Wed, 31 Dec at 09:00 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

🎸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

Marc Douglas Berardo and Grace Morrison in Annapolis, MD

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

G. Love & Special Sauce - Lemonade 20th Anniversary Tour with Special Guest MAKUA

 Wed, 04 Feb at 08:00 pm Rams Head On Stage

John Moreland, Patterson Hood in Annapolis

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

The Billy Price Band & The Chris O'Leary Band (Matinee)

Sun, 01 Feb at 01:00 pm Rams Head On Stage

The Annapolis Opry

 Sun, 11 Jan at 02:00 pm St. Margaret's Episcopal Church

Naptown Brass Band Mardi Gras at Rams Head!!!

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

Honky Tonk Casanovas Comes to The Annapolis Smokehouse

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

Hyland Brothers Live @ Stan & Joe’s

 Wed, 21 Jan at 09:00 pm Stan and Joe's Saloon

Annapolis M**der Mystery: Catch the Killer!

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

G. Love & Special Sauce- Lemonade 20th Anniversary Tour with Special Guest MAKUA

 Tue, 03 Feb at 08:00 pm Rams Head On Stage

Black Violin

 Fri, 27 Feb Rams Head On Stage

Reverend Horton Heat & Black Joe Lewis

 Tue, 07 Apr Rams Head On Stage

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

 Tue, 05 May 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

Black Violin: Full Circle at Rams Head On Stage

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

Penny and Sparrow in Annapolis

 Thu, 09 Apr at 08:00 pm Rams Head On Stage

Sue Foley

 Thu, 12 Mar Rams Head On Stage

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

 Thu, 30 Oct at 08:00 pm Annapolis Free