Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

Pure Prairie League in Annapolis

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

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 06:30 pm Rams Head On Stage

The Moonshiners Ball 2025 A Cocktail Party for the SPCA and Slade Child Foundation.

 Sun, 07 Dec at 05:00 pm Latitude 38 Annapolis

Keb' Mo' in Annapolis

 Fri, 21 Nov at 08:00 pm Maryland Hall

Marshall Crenshaw: 40+ Years in Showbiz

 Fri, 14 Nov at 08:00 pm Rams Head On Stage

Rams Head Presents Natalie Merchant w/ Erik Della Penna: Autumn Acoustic Tour - Maryland Hall

 Sun, 23 Nov at 07:30 pm Maryland Hall

Will Hoge Band w/ July Moon

Sun, 16 Nov at 08:00 pm Rams Head On Stage

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 06:30 pm Rams Head On Stage

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 09:30 pm Rams Head On Stage

November Film Club - "For All Have Sinned"

 Fri, 21 Nov at 06:00 pm AND Creative Studio USD 18

Sister Hazel (matinee)

Sat, 15 Nov at 01:00 pm Rams Head On Stage

Siren's Call

 Fri, 28 Nov at 05:00 pm The Westin Annapolis Free

Atlanta Rhythm Section in Annapolis

 Sat, 06 Dec at 08:00 pm Rams Head On Stage

2025 FRA 24 Holiday Party

 Sat, 06 Dec at 06:00 pm Fleet Reserve Club Of Annapolis USD 66

Last Train Home

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

Siren's Call

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

Siren's Call

 Fri, 12 Dec at 05:00 pm The Westin Annapolis Free

Encore Chorale Annapolis - 12/6 Concert

 Sat, 06 Dec at 02:00 pm Maryland Hall Free

Hotel Paradise (Dance Area!)

Sun, 30 Nov at 07:00 pm Rams Head On Stage

Footworks Percussive Dance Ensemble

 Sat, 15 Nov at 03:00 pm Unitarian Universalist Church of Annapolis

Holiday Pops at Maryland Hall

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

Marshall Crenshaw at Rams Head On Stage

 Fri, 14 Nov at 08:00 pm Rams Head On Stage

The Brit Pack at Rams Head On Stage

 Sat, 22 Nov at 08:00 pm Rams Head On Stage

Chris Isaak in Annapolis

 Sun, 07 Dec at 08:00 pm Maryland Hall

Siren's Call

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

Jon McLaughlin & Friends: Home For The Holidays

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

Encore ROCKS Annapolis - 12/1 Concert

 Mon, 01 Dec at 07:00 pm Maryland Hall Free

Paapa-Berchie, Live Music Experience

 Sat, 22 Nov at 07:30 pm Annapolis Mall USD 34

Acoustic Alchemy

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

Will Hoge at Rams Head On Stage

 Sun, 16 Nov at 08:00 pm Rams Head On Stage

Live Arts Maryland Presents Music of the Spheres

 Sat, 15 Nov at 07:30 pm Maryland Hall USD 39

Tides & Tunes

 Tue, 11 Nov at 05:00 pm The Westin Annapolis Free

Laura Tsaggaris (Matinee)

Sat, 06 Dec at 01:00 pm Rams Head On Stage

Colin Hay in Annapolis

 Tue, 11 Nov at 08:00 pm St. John's College - Francis Scott Key Auditorium

Tides & Tunes

 Tue, 18 Nov at 05:00 pm The Westin Annapolis Free

The Brit Pack: British Invasion & More!

 Sat, 22 Nov at 08:00 pm Rams Head On Stage

The Carole King & James Taylor Story

 Sat, 15 Nov at 08:00 pm Rams Head On Stage

Jim Messina and his band The Road Runners

 Tue, 25 Nov at 08:00 pm Rams Head On Stage

Jimmie's Chicken Shack Holidaze Show

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

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

 Sat, 15 Nov at 07:00 pm Stan & Joe's Saloon USD 23

The Doug Segree Band at 49 West

Mon, 17 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

Siren's Call

 Fri, 14 Nov at 05:00 pm The Westin Annapolis Free

Live Dead and Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers

 Sun, 23 Nov at 08:00 pm Rams Head On Stage

Deadgrass, Bluegrass Covers of The Grateful Dead

 Tue, 11 Nov at 07:30 pm Annapolis Mall USD 34

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

 Fri, 14 Nov at 07:00 pm Stan & Joe's Saloon USD 23

Navy Midshipmen Tailgate Party

 Sat, 15 Nov at 10:00 am The Westin Annapolis Free

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

 Sat, 13 Dec at 08:30 pm Rams Head On Stage

Shakey Graves

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

Tides & Tunes

 Tue, 02 Dec at 05:00 pm The Westin Annapolis Free

Live Arts Maryland presents Bluegrass Nutcracker

 Fri, 05 Dec at 07:30 pm Annapolis Mall USD 34

Siren's Call

 Fri, 21 Nov at 05:00 pm The Westin Annapolis Free

Sister Hazel in Annapolis

 Sat, 15 Nov at 01:00 pm Rams Head On Stage

U2topia: The Mid-Atlantic U2 Tribute Band

Fri, 28 Nov at 08:00 pm Rams Head On Stage

SOD-O Holiday Party

 Sat, 06 Dec at 06:00 pm Acqua al 2 - Annapolis USD 0 to 100

Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"

 Sat, 15 Nov at 11:00 am Anne Arundel County Public Library (Eastport-Annapolis Neck Library)

The Martin Sexton Abbey Road Show at Rams Head On Stage

 Fri, 21 Nov at 08:00 pm Rams Head On Stage

Be Still and Know: A Journey Into Sound & Soul

 Fri, 05 Dec at 06:30 pm Unity by the Bay USD 39

PARKING: Military Bowl

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

Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

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

Tides & Tunes

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

Rams Head Presents Chris Isaak - Annapolis, MD

 Sun, 07 Dec at 08:00 pm Maryland Hall

Peter Mayer: A Stars and Promises Christmas 2025

Thu, 11 Dec at 08:00 pm Rams Head On Stage

Joshua Redman Quartet

 Sun, 16 Nov at 07:00 pm 801 Chase St, Annapolis, MD, United States, Maryland 21401

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

Tides & Tunes

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

Live @ Stan & Joe's

 Sat, 15 Nov at 09:45 pm Stan and Joe's Saloon

Avery*Sunshine

 Sun, 18 Jan at 08:00 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

Paint Night @ NEO PIZZA - Annapolis

 Thu, 20 Nov at 06:00 pm Neo Pizza & Taphouse USD 40

Cash Unchained – The Ultimate Johnny Cash Tribute

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

Tides & Tunes

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

Paint Night @ NEO PIZZA - Annapolis

 Wed, 12 Nov at 06:00 pm Neo Pizza & Taphouse USD 40

Lights Parade Dinner Cruise with Ken's Creative Kitchen

 Sat, 13 Dec at 05:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Danny Burns Band

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

Vienna Teng at Rams Head On Stage

 Thu, 20 Nov Rams Head On Stage

Candlelight: Tribute to The Beatles | Annapolis

 Thu, 20 Nov at 06:30 pm Hubbard Hall (Annapolis, Maryland)

BRAHMS & ICE CREAM: A Chamber Concert for Piano & Strings

 Sat, 22 Nov at 03:00 pm 801 Chase St Ste 204, Annapolis, MD, United States, Maryland 21401

Military Bowl

 Fri, 26 Dec Navy Marine Corps Memorial Stadium

Candlelight: Tribute to Fleetwood Mac | Annapolis

 Thu, 20 Nov at 06:30 pm Maryland Hall

Seth Mitchell Band w/ Shannon Leigh

 Tue, 11 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

Pressing Strings

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

Kashmir - The Led Zeppelin Experience

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

Naptown 2 NOLA Album Release Party with Papa Lebas & Gumbo Ya Ya

 Tue, 18 Nov at 08:00 pm Rams Head On Stage

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

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

Billy Price Band

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

Crushed Glass Ornaments @ NEO Pizza w/MD Craft Parties

 Tue, 18 Nov at 06:00 pm Neo Pizza Annapolis USD 55

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

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

Ram's Head on Stage

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

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

 Sat, 13 Dec at 03:30 pm Rams Head On Stage

Scorpion Rose

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

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

Annapolis Jazz & Roots Festival Freedom Choir led by Elizabeth Melvin

 Sun, 16 Nov at 03:00 pm St. Luke's Eastport

The Magic of Cinema - April 18, 2026

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

Tides & Tunes

 Tue, 25 Nov at 05:00 pm The Westin Annapolis Free

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 SQRRL! Holiday (Matinee)

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

A Very Merry Drag Brunch

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

A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)

Thu, 04 Dec at 06:30 pm Rams Head On Stage

Chris Isaak

 Sat, 06 Dec at 07:00 pm Maryland Hall For The Creative Arts