Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

Undead Mile Run – Annapolis, MD

 Sat, 25 Oct at 08:00 pm Annapolis, Annapolis, Maryland

Najee in Annapolis

 Sun, 09 Nov at 07:30 pm Rams Head On Stage

Pure Prairie League in Annapolis

 Fri, 05 Dec 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

Keb' Mo' in Annapolis

 Fri, 21 Nov at 08:00 pm Maryland Hall

Najee in Annapolis

 Sun, 09 Nov at 04:30 pm Rams Head On Stage

Caliente Karaoke - Powered by KJ DJ Ben

 Sat, 25 Oct at 08:00 pm Caliente Grill Free

2025 Shore Party

 Sat, 01 Nov at 05:00 pm Safe Harbor Annapolis

Richard Thompson in Annapolis

 Sun, 02 Nov at 07:30 pm St. John's College - Francis Scott Key Auditorium

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

Atlanta Rhythm Section in Annapolis

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

Annapolis Halloween Rooftop Party : Haunted Heights

 Fri, 31 Oct at 08:00 pm Metropolitan Kitchen & Lounge Free

Dancing Night at Caliente Grill - Bachata Class & Social Dance

 Fri, 24 Oct at 08:00 pm Caliente Grill Free

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

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

Thomas Dolby - The Iconic 80s at Rams Head On Stage

 Fri, 24 Oct at 08:00 pm Rams Head On Stage

Siren's Call

 Fri, 24 Oct at 05:00 pm The Westin Annapolis Free

Wishbone Ash: Wishlist Tour

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

Navy Midshipmen Tailgate Party

 Sat, 25 Oct at 01:30 pm The Westin Annapolis Free

Chris Isaak in Annapolis

 Sun, 07 Dec at 08:00 pm Maryland Hall

Marshall Crenshaw: 40+ Years in Showbiz

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

Siren's Call

 Fri, 31 Oct at 05:00 pm The Westin Annapolis Free

Eli Lev at Unity by the Bay Church

 Fri, 07 Nov at 07:00 pm Unity by the Bay (Maryland)

Macy Gray at Rams Head On Stage

 Sun, 02 Nov at 08:30 pm Rams Head On Stage

Siren's Call

 Fri, 07 Nov at 05:00 pm The Westin Annapolis Free

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

 Sun, 23 Nov at 07:30 pm Maryland Hall

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 Brit Pack: The Ultimate British Music Experience

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

GA-20 and Black Joe Lewis & The Honeybears

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

Siren's Call

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

Navy Midshipmen Tailgate Party

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

Will Hoge Band w/ July Moon

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

Ketch Secor

 Sun, 02 Nov at 07:00 pm Rams Head On Stage

Colin Hay in Annapolis

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

Siren's Call

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

The Doug Segree Band at 49 West

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

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

Tall Tall Trees at Rams Head On Stage

 Sat, 25 Oct Rams Head On Stage

Will Hoge at Rams Head On Stage

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

Crack the Sky

 Sat, 01 Nov at 08:00 pm Rams Head On Stage

Siren's Call

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

Last Train Home

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

Haunted Harbour Day 2025

 Sat, 25 Oct at 10:00 am 2512 A Solomons Island Road, Annapolis, MD 21401

Tall Tall Trees

 Sat, 25 Oct at 05:00 pm Rams Head On Stage - Annapolis

Sunday Fun Day & Art Walk in Downtown Annapolis

 Sat, 01 Nov at 01:00 pm 172 Green St USD 29 to 50

Don Giovanni

 Fri, 31 Oct at 07:30 pm Maryland Hall

Siren's Call

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

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 02 Nov at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Shakey Graves

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

Peter Mayer: A Stars and Promises Christmas 2025

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

Siren's Call

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

Dan Navarro at Rams Head On Stage

 Thu, 06 Nov at 08:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 26 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Freddy Jones Band

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

Tides & Tunes

 Tue, 21 Oct at 05:00 pm The Westin Annapolis Free

Dan Navarro w/ Jesse Lynn Madera

 Thu, 06 Nov at 08:00 pm Rams Head On Stage

Signature Series: Darkness to Light

 Sat, 08 Nov at 07:30 pm Maryland Hall for the Creative Arts

Dracula: A Comedy of Terrors

 Fri, 24 Oct at 08:00 pm 108 East St, Annapolis, MD, United States, Maryland 21401

Light House Bountiful Harvest ~ Costumes & Cocktails

 Fri, 24 Oct at 07:00 pm The Atreeum at Soaring Timbers

The Jerry Douglas Band at Rams Head On Stage

 Wed, 05 Nov at 08:00 pm Rams Head On Stage

Siren's Call

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

Carbon Leaf

 Fri, 12 Dec at 07:00 pm Rams Head On Stage

Pete Correale

 Thu, 06 Nov at 07:00 pm Rams Head On Stage

Live @ Stan & Joe's

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

Signature Series: Darkness to Light

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

Vienna Teng at Rams Head On Stage

 Thu, 20 Nov Rams Head On Stage

The Moment Live Band & Show

 Sat, 01 Nov at 07:00 pm 1707 Forest Dr USD 23

The Marshall Morlock Band

 Sun, 26 Oct at 07:00 pm Rams Head On Stage

PARKING: Military Bowl

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

Live Arts Maryland presents the Phantom of the Opera

 Thu, 30 Oct at 07:00 pm St. Anne's Parish Free

Paapa-Berchie, Live Music Experience

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

Raynes

 Wed, 29 Oct 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

Laura Tsaggaris (Matinee)

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

Taste of Fall on West Street

 Sun, 09 Nov at 02:00 pm 53 West St USD 7 to 82

Four80East

 Fri, 24 Oct at 07:00 pm Rams Head On Stage

Live Arts Maryland Presents Music of the Spheres

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

Harvest Festival - FREE

 Sat, 25 Oct at 10:00 am Roger W "Pip" Moyer Community Recreation Center at Truxtun Park, 273 Hilltop Ln, Annapolis, MD, United States, Maryland 21403

The Jerry Douglas Band

 Tue, 04 Nov at 07:00 pm Rams Head On Stage

Tides & Tunes

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

Military Bowl

 Fri, 26 Dec Navy Marine Corps Memorial Stadium

Annapolis True Crime: Murder at Middleton

 Thu, 30 Oct at 06:30 pm Middleton Tavern

Cruise to St. Michaels OysterFest

 Sat, 25 Oct at 09:15 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Acoustic Alchemy

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

Jarrod Lawson concert at Rams Head On Stage

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

Pete Correale at Rams Head On Stage

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

Danny Burns Band

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

Tides & Tunes

 Tue, 18 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

Jim Messina and his band The Road Runners

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

Kashmir - The Led Zeppelin Experience

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

LIVE MUSIC with Bravenoise

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

Ram's Head on Stage

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

Scorpion Rose

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

The Brit Pack at Rams Head On Stage

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

Zumba class with Diana Bobrow

 Tue, 21 Oct at 06:30 pm 2158 Renard Ct Free

Wishbone Ash

 Fri, 07 Nov at 07:00 pm Rams Head On Stage

Candlelight: Halloween Classics | Annapolis

 Thu, 30 Oct at 08:45 pm Maryland Hall

Sister Hazel (matinee)

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

Marshall Crenshaw at Rams Head On Stage

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