Entertainment events in Annapolis

Check out happening entertainment events all around Annapolis, MD

Barktoberfest Annapolis 2025

 Sat, 04 Oct at 11:30 am 1906 Towne Centre Blvd USD 0 to 13

Undead Mile Run – Annapolis, MD

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

Annapolis Skelly Run

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

Najee in Annapolis

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

Atlanta Rhythm Section in Annapolis

 Sat, 06 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

Pure Prairie League in Annapolis

 Fri, 05 Dec 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

Yasmin Williams at Rams Head On Stage

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

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

Najee in Annapolis

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

Keb' Mo' in Annapolis

 Fri, 21 Nov at 08:00 pm Maryland Hall

Karaoke Night - Caliente Grill

 Fri, 03 Oct at 08:00 pm Caliente Grill Free

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

 Fri, 10 Oct 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

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

Band of a Thousand Names

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

The Moonshiners Ball 2025 A Cocktail party and fundraiser for the SPSA

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

Siren's Call

 Fri, 03 Oct at 05:00 pm The Westin Annapolis Free

American Aquarium in Annapolis

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

Party in the Port

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

Siren's Call

 Fri, 10 Oct at 05:00 pm The Westin Annapolis Free

Close Enemies

 Fri, 10 Oct 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

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

 Fri, 10 Oct at 07:30 pm Maryland Hall for the Creative Arts

Signature Series: Darkness to Light

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

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

 Mon, 06 Oct at 07:00 pm Rams Head On Stage

Siren's Call

 Fri, 17 Oct at 05:00 pm The Westin Annapolis Free

Acoustic Alchemy

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

Wishbone Ash: Wishlist Tour

 Sat, 08 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, 24 Oct at 05:00 pm The Westin Annapolis Free

Greg Hawkes and Eddie Japan

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

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

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

Eli Lev at Unity by the Bay Church

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

Four80East

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

Taylor Swift The Life of A Showgirl Album Drop Party

 Fri, 03 Oct at 04:30 pm Prism Annapolis USD 45

Cruise to St. Michaels OysterFest

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

Live Arts Maryland Presents Music of the Spheres

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

Delegate Dylan's Pizza Party!

 Thu, 09 Oct at 06:00 pm Eastport Democratic Club

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

The Annapolis Art Party: Five Years of Color

 Sat, 11 Oct at 05:00 pm AND Creative Studio Free

The Secret Sisters

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

Noelle & Jeff Full Band!

 Fri, 03 Oct at 10:00 pm Middleton Tavern

Lene Lovich at Rams Head On Stage

 Wed, 01 Oct Rams Head On Stage

Siren's Call

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

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

Marshall Crenshaw at Rams Head On Stage

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

Technicolor Motor Home

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

The Steve Morse Band

 Thu, 16 Oct at 08:00 pm Rams Head On Stage

Navy Midshipmen Tailgate Party

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

Annapolis Midnight Mile Vampire Run

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

Siren's Call

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

Will Hoge w/ July Moon

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

Siren's Call

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

Colin Hay in Annapolis

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

American Aquarium at Rams Head On Stage

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

The Amish Outlaws

 Thu, 16 Oct at 07:00 pm Rams Head On Stage

Tide's & Tunes

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

Haunted Harbour Day 2025

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

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

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

Rooftop Thursdays with Andrew Bell

 Thu, 02 Oct at 06:00 pm Blackwall Hitch - Annapolis

Crack the Sky

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

The Martin Sexton Abbey Road Show at Rams Head On Stage

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

Dan Navarro w/ Jesse Lynn Madera

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

NJPC Feed the Mids! Navy vs Air Force!!

 Sat, 04 Oct at 07:00 am Navy–Marine Corps Memorial Stadium

Crack the Sky (Matinee)

Sun, 02 Nov at 01:00 pm Rams Head On Stage

Candlelight: Halloween Classics | Annapolis

 Thu, 30 Oct at 08:45 pm Maryland Hall

Tides & Tunes

 Tue, 07 Oct at 05:00 pm The Westin Annapolis Free

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

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

 Fri, 03 Oct 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

Sunday Fun Day & Art Walk in Downtown Annapolis

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

Close Enemies feat. Tom Hamilton of Aerosmith

 Sat, 11 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

Tom Sandoval

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

Annapolis Smokehouse & Tavern

 Fri, 03 Oct at 08:30 pm Annapolis, MD

Tab Benoit

 Sat, 06 Dec at 07:00 pm Rams Head On Stage

Tides & Tunes

 Tue, 14 Oct at 05:00 pm The Westin Annapolis Free

Katie Pruitt: Time Wasn't Wasted Tour w/ Jess Nolan

 Wed, 15 Oct at 08:00 pm Rams Head On Stage

Rams Head Presents Chris Isaak - Annapolis, MD

 Sun, 07 Dec at 08:00 pm Maryland Hall

Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

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

Navy Midshipmen Tailgate Party

 Sat, 04 Oct at 08:00 am The Westin Annapolis Free

Steven Page at Rams Head On Stage

 Sun, 12 Oct at 01:00 pm Rams Head On Stage

Rooftop Thursdays with Madisun Bailey

 Thu, 16 Oct at 06:00 pm Blackwall Hitch - Annapolis

Noelle & Jeff Full Band!

 Fri, 07 Nov at 10:00 pm Middleton Tavern

Marshall Crenshaw: 40+ Years in Showbiz

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

Dan Navarro at Rams Head On Stage

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

First Sunday Arts Festival

Sun, 05 Oct at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Cruise to OysterFest in St. Michaels

 Sat, 25 Oct at 09:00 am 1 Dock St, Annapolis, MD, United States, Maryland 21401

Marching Band Formal Parade

Fri, 24 Oct at 04:20 pm Worden Field

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

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

Tides & Tunes

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

Signature Series: Darkness to Light

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

Jon McLaughlin & Friends: Home For The Holidays

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

Tides & Tunes

 Tue, 28 Oct at 05:00 pm The Westin Annapolis Free

LIVE MUSIC with Rick & The Revolving Doors

 Sat, 04 Oct at 09:00 pm Blackwall Hitch - Annapolis

ONO - One Night Only Band at Blackwall Hitch Annapolis

 Fri, 10 Oct at 08:30 pm Blackwall Hitch - Annapolis