Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

War in Annapolis

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

War in Annapolis

 Thu, 25 Sep at 08:00 pm Rams Head On Stage

35th Annual Kunta Kinte Heritage Festival

Sat, 13 Sep at 10:00 am Navy–Marine Corps Memorial Stadium

The Wallflowers, Brother Elsey in Annapolis

 Tue, 23 Sep at 08:00 pm Rams Head On Stage

Signature Series: A New World with Pablo Sainz-Villegas, guitar

 Sat, 11 Oct at 07:30 pm Maryland Hall for the Creative Arts

Undead Mile Run – Annapolis, MD

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

Peter White, Mindi Abair, Vincent Ingala in Annapolis

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

NILS, Jeff Kashiwa, Nils in Annapolis

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

3hr Sunset Cruise w/ Live Entertainment from: KEVIN LEE

 Sat, 20 Sep at 06:00 pm Annapolis, MD

Pure Prairie League in Annapolis

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

10,000 Maniacs

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

Nils at Rams Head On Stage

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

10000 Maniacs at Rams Head On Stage

 Sat, 13 Sep Rams Head On Stage

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

 Fri, 12 Sep at 06:00 pm Calvert Street Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 12 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Keb' Mo' in Annapolis

 Fri, 21 Nov at 08:00 pm Maryland Hall

Maysa (8:30 PM)

 Sat, 20 Sep at 08:30 pm Rams Head On Stage

Chris Standring in Annapolis

 Wed, 10 Sep at 08:00 pm Rams Head On Stage

Chris Standring in Annapolis

 Wed, 10 Sep at 08:00 pm Rams Head On Stage

10,000 Maniacs

 Sun, 14 Sep at 07:30 pm Rams Head On Stage

Hermans Hermits

 Sat, 27 Sep Rams Head On Stage

Skerryvore in Annapolis

 Mon, 08 Sep at 08:00 pm Rams Head On Stage

*SOLD OUT* The Ocean Blue w/ Brian Tighe of The Hang Ups

 Fri, 10 Oct at 08:00 pm Rams Head On Stage

Annapolis Fall Italian Festa

 Sun, 21 Sep at 10:00 am 620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 21 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 07 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Technicolor Motor Home

 Sun, 12 Oct at 08:00 pm Rams Head On Stage

Casey Abrams

 Sun, 14 Sep at 07:00 pm Rams Head On Stage

The Robert Cray Band in Annapolis

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

Richard Thompson in Annapolis

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

Jeff Muller & Friends present Canciones de las Americas

 Fri, 12 Sep at 07:30 pm 49 West Coffeehouse, Winebar & Gallery

WAR: 50th Anniversary Tour of Why Can't We Be Friends?

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

Greg Hawkes at Rams Head On Stage

 Fri, 03 Oct at 08:00 pm Rams Head On Stage

Casey Abrams in Annapolis

 Mon, 15 Sep at 08:00 pm Rams Head On Stage

The Dave Matthews Tribute Band

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

Robert Cray in Annapolis

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

RiverBay Rocking End of Summer Jam

Sat, 13 Sep at 05:00 pm 1145 RiverBay Rd in Cape

Crack the Sky

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

Najee in Annapolis

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

Salsa & Sangria in Downtown Annapolis

 Fri, 12 Sep at 05:00 pm 172 Green St USD 93 to 157

Close Enemies

 Sat, 11 Oct at 08:00 pm Rams Head On Stage

Greg Hawkes w/ Eddie Japan Performing the Music of The Cars

 Fri, 03 Oct at 08:00 pm Rams Head On Stage

Sheena Easton in Annapolis

 Tue, 09 Sep at 08:00 pm Rams Head On Stage

Atlanta Rhythm Section in Annapolis

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

Steve Morse Band

 Wed, 15 Oct at 07:00 pm Rams Head On Stage

LIVE MUSIC: The Freebyrds

 Sat, 06 Sep at 06:00 pm Rams Head Tavern Annapolis

American Aquarium in Annapolis

 Wed, 08 Oct at 08:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

Party in the Port

 Sat, 11 Oct at 06:00 pm 317 First St, Annapolis, MD, United States, Maryland 21403

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 28 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Acoustic Alchemy

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

DIRTY HEADS w. Ballyhoo! & Wheeland Brothers

 Fri, 12 Sep at 06:00 pm 44 Calvert St, Annapolis, MD 21401-1930, United States

Last Annapolis City Dock Tango Septemeber 2025

 Sat, 06 Sep at 07:00 pm Susan Campbell Park

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 05 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

BAYGRASS 2025: Annapolis Baygrass Music Festival 9/20-21

 Sat, 20 Sep at 10:00 am 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

Tango Reo Quintet at Annapolis City Dock Tango

 Sat, 06 Sep at 08:00 pm Annapolis City Dock

Maysa

 Fri, 19 Sep at 07:00 pm Rams Head On Stage

The Amish Outlaws return to Rams Head On Stage

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

Dirty Heads

 Thu, 11 Sep at 07:00 pm Calvert Street Stage

Steep Canyon Rangers at Maryland Hall for the Creative Arts

 Thu, 11 Sep at 08:00 pm Maryland Hall for the Creative Arts

The Dustbowl Revival

 Sat, 06 Sep Rams Head On Stage

Rams Head Presents Steep Canyon Rangers - Maryland Hall - Annapolis, MD

 Thu, 11 Sep at 08:00 pm Maryland Hall

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

 Fri, 26 Sep at 06:00 pm Charthouse Restaurant Annapolis

Annapolis Skelly Run

 Sat, 04 Oct at 08:00 pm Annapolis, Annapolis, Maryland

The Ocean Blue w/ Brian Tighe of The Hang Ups (2nd Night Added!)

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

SAT 9/20/25: BATMAN DAY 2025 AT THIRD EYE

 Sat, 20 Sep at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

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

 Sun, 23 Nov at 07:30 pm Maryland Hall

Ari Hest & Chris Trapper

 Wed, 24 Sep at 08:00 pm Rams Head On Stage

Danny Burns Band

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

The Australian Bee Gees Show: A Tribute to The Bee Gees (8:00PM)

 Sun, 05 Oct at 08:00 pm Rams Head On Stage

Pat McGee Band

 Sat, 06 Sep Rams Head On Stage

Songbird Showcase w/Mac Heat "Lite"

 Wed, 10 Sep at 07:00 pm 49 West Coffeehouse Wine Bar & Gallery

Four80East

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

New Member Party at Porsche Annapolis

 Sat, 27 Sep at 09:00 am Porsche Annapolis

Boatyard Beach Bash

 Sat, 20 Sep at 04:00 pm 723 2nd St, Annapolis, MD, United States, Maryland 21403

Pat McGee & Friends : All Request Show (Matinee)

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

Marshall Crenshaw: 40+ Years in Showbiz

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

Chris Isaak in Annapolis

 Sun, 07 Dec at 08:00 pm Maryland Hall

Al Jardine and The Pet Sounds Band

 Fri, 12 Sep at 07:00 pm Maryland Hall For The Creative Arts

Rooftop Thursdays with Dave Tieff

 Thu, 11 Sep at 06:00 pm Blackwall Hitch - Annapolis

Greg Hawkes and Eddie Japan

 Thu, 02 Oct at 07:00 pm Rams Head On Stage

Yasmin Williams at Rams Head On Stage

 Thu, 02 Oct at 08:00 pm Rams Head On Stage

Shaun Cassidy: The Road To Us Tour (Annapolis, MD)

 Sat, 18 Oct at 08:00 pm 33 West St, Annapolis, MD, United States, Maryland 21401

Herman's Hermits Starring Peter Noone (7:30PM)

 Sun, 28 Sep at 07:30 pm Rams Head On Stage

Noelle & Jeff Full Band!

 Fri, 03 Oct at 10:00 pm Middleton Tavern

Blues & Gold and Bravo Zulu Brass Band at Radford Terrace

 Thu, 25 Sep at 07:00 pm Radford Terrace

Annapolis Songwriters Fesitival

 Thu, 11 Sep at 05:00 pm Rams Head Tavern Annapolis

Dustbowl Revival w/ Chris Kasper

 Sun, 07 Sep at 08:00 pm Rams Head On Stage

Al Jardine and The Pet Sounds Band

 Sat, 13 Sep at 08:00 pm Maryland Hall

West Annapolis Oktoberfest 2025

 Sun, 28 Sep at 11:00 am Annapolis Street, Annapolis, MD, United States, Maryland 21401

Joe Pug at Rams Head On Stage

 Sat, 27 Sep at 08:00 pm Rams Head On Stage

Annapolis Midnight Mile Vampire Run

 Sat, 11 Oct at 06:00 pm Annapolis, Annapolis, Maryland

Scandalous Annapolis

 Sat, 06 Sep at 07:30 pm 188 Main St, Annapolis, MD 21401-2008, United States

Siren's Call

 Fri, 19 Sep at 05:00 pm The Westin Annapolis Free

Marshall Crenshaw at Rams Head On Stage

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

Najee in Annapolis

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

Diamonds Are Forever

 Fri, 19 Sep at 07:30 pm Innovation Academy Auditorium

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

 Fri, 19 Sep at 07:00 pm Stan & Joe's Saloon USD 23

Dinner Under the Stars

Wed, 10 Sep at 05:00 pm West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401

Zumba class with Diana Bobrow

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