Annapolis Arts Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

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

Maryland Hall for the Creative Arts 11 Oct 2025

Undead Mile Run – Annapolis, MD

Annapolis, Annapolis, Maryland 25 Oct 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

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

Annapolis, MD 20 Sep 2025

10,000 Maniacs

Rams Head On Stage 13 Sep 2025

Dirty Heads, Ballyhoo!, Wheeland Brothers in Annapolis

Calvert Street Stage 12 Sep 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 12 Oct 2025

Maysa (8:30 PM)

Rams Head On Stage 20 Sep 2025

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

Rams Head On Stage 10 Oct 2025

10,000 Maniacs

Rams Head On Stage 14 Sep 2025

Skerryvore in Annapolis

Rams Head On Stage 8 Sep 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 7 Sep 2025

Family Art Nights at ArtFarm

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 19 Sep 2025

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

Rams Head On Stage 3 Oct 2025

Ballet Theatre of Maryland - The Nutcracker at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 13 Dec 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 28 Sep 2025

Giselle at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 17 Oct 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 2 Nov 2025

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

1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 20 Sep 2025

Ballet in the Garden at the Hammond Harwood House

Hammond-Harwood House 21 Sep 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 5 Oct 2025

Annapolis Skelly Run

Annapolis, Annapolis, Maryland 4 Oct 2025

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

Maryland Hall 11 Sep 2025

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

Maryland Hall 23 Nov 2025

Al Jardine at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 13 Sep 2025

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

Rams Head On Stage 9 Oct 2025

Annapolis Fall Italian Festa

620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

Mixed Media Encaustic Collage Workshop

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 14 Sep 2025

SAT 9/13/25: ESCAPE #1 Signing with writer RICK REMENDER

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 13 Sep 2025

Afternoon "Tea" — An Ideal Husband Talk Back

108 East St, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

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

33 West St, Annapolis, MD, United States, Maryland 21401 18 Oct 2025

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

Rams Head On Stage 28 Sep 2025

Citizens & Sovereigns Book Club

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 9 Sep 2025

Najee in Annapolis

Rams Head On Stage 9 Nov 2025

Dustbowl Revival w/ Chris Kasper

Rams Head On Stage 7 Sep 2025

Siren's Call

The Westin Annapolis 19 Sep 2025

People in Portraits

19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 14 Sep 2025

Colin Hay in Annapolis

St. John's College - Francis Scott Key Auditorium 11 Nov 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 26 Oct 2025

Siren's Call

The Westin Annapolis 26 Sep 2025

Ballet Theatre of Maryland: Giselle

Maryland Hall For The Creative Arts 16 Oct 2025

Siren's Call

The Westin Annapolis 12 Sep 2025

Dan Navarro w/ Jesse Lynn Madera

Rams Head On Stage 6 Nov 2025

Full Moon Celebration - October

Unitarian Universalist Church of Annapolis 3 Oct 2025

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 7 Sep 2025

Kim Hovell - Paint & Paddle

655 Americana Dr, Annapolis, MD 21403, United States 21 Sep 2025

Keb Mo at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 21 Nov 2025

Siren's Call

The Westin Annapolis 3 Oct 2025

Herman's Hermits

Rams Head On Stage 27 Sep 2025

NARI After 5

Bright Light Design Center 9 Sep 2025

Mixed Media Encaustic Collage Workshop

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 12 Oct 2025

Siren's Call

The Westin Annapolis 10 Oct 2025

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 8 Nov 2025

Pumpkin Walk

19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 24 Oct 2025

Siren's Call

The Westin Annapolis 17 Oct 2025

Opera Up-Close featuring Katerina Burton

Asbury United Methodist Church 5 Oct 2025

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

Rams Head On Stage 15 Oct 2025

Ballet Theatre of Maryland presents "Giselle"

Maryland Hall 18 Oct 2025

Chris Isaak

Maryland Hall For The Creative Arts 6 Dec 2025

Rams Head Presents Chris Isaak - Annapolis, MD

Maryland Hall 7 Dec 2025

The Annapolis Art Party: Five Years of Color

1851 McGuckian Street, Annapolis, MD, United States, Maryland 21401 11 Oct 2025

Official Annapolis Baygrass Kickoff Party: Fitzkee Brothers & Wicked Sycamore

Maryland Hall 19 Sep 2025

Mini Performance of Giselle by Ballet Theatre of Maryland.

Maryland Hall 17 Oct 2025

50-hr Yin Training & Immersion

119 Hillsmere Drive, Annapolis, MD, United States, Maryland 21403 17 Oct 2025

Come Out and Play with Naleighna Kai and the Tribe

210 Holiday Ct 31 Oct 2025

Annapolis Baygrass Festival TAP TAKEOVER at Stan & Joe's

Stan and Joe's Saloon 13 Sep 2025

Ballet Theatre of Maryland: The Nutcracker

Maryland Hall For The Creative Arts 12 Dec 2025

Are You Really Listening? What to Say When Supporting Others

2158 Renard Ct 4 Dec 2025

Songwriters In The Round

Rams Head On Stage 11 Sep 2025

Natalie Merchant at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 23 Nov 2025

Tides & Tunes

The Westin Annapolis 9 Sep 2025

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 7 Nov 2025

Sacred Abundance Workshop with Rev. Sarah Phillips

4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409 18 Sep 2025

The Carole King & James Taylor Story

Rams Head On Stage 15 Nov 2025

Siren's Call

The Westin Annapolis 31 Oct 2025

Siren's Call

The Westin Annapolis 24 Oct 2025

7th Annual Bubbly Bridal Expo & 1000+ Gown Sale!

Graduate Annapolis 23 Nov 2025

The Crabtown Frolic

19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 27 Sep 2025

Songbird Showcase w/Mac Heat "Lite"

49 West Coffeehouse Wine Bar & Gallery 10 Sep 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Full Moon Celebration - November

Unitarian Universalist Church of Annapolis 7 Nov 2025

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

Maryland Hall for the Creative Arts 10 Oct 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 19 Oct 2025

Chris Isaak at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 7 Dec 2025

Tides & Tunes

The Westin Annapolis 16 Sep 2025

The Brit Pack: The Ultimate British Music Experience

Rams Head On Stage 22 Nov 2025

Key School Soccer Clinic

2705 Carrollton Rd, Annapolis, MD 21403-4200, United States 13 Sep 2025

Captain Curiosity Show

89 Bennion Rd, Annapolis, MD 21402-1119, United States 20 Sep 2025

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 7 Dec 2025

Naked Blue at 49 West with Special Guest Larry Ahearn

49 West Coffeehouse, Winebar & Gallery 15 Sep 2025

Casey Abrams & Friends featuring Dylan Chambers and Hunter

Rams Head On Stage 15 Sep 2025

Siren's Call

The Westin Annapolis 7 Nov 2025

Steep Canyon Rangers

Maryland Hall For The Creative Arts 10 Sep 2025

Annapolis First Sunday Arts Festival w/ The Accidental Poet

West St, Annapolis, MD 21401, United States 7 Sep 2025

Tides & Tunes

The Westin Annapolis 23 Sep 2025

Cash Unchained – The Ultimate Johnny Cash Tribute

Rams Head On Stage 22 Jan 2026

Will Hoge w/ July Moon

Rams Head On Stage 16 Nov 2025