Annapolis Music Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Chris Isaak in Annapolis

Maryland Hall 7 Dec 2025

Annapolis Chocolate Binge Festival

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

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

Latitude 38 Annapolis 7 Dec 2025

Family Karaoke Sunday - Powered by DJ KJ Ben

Caliente Grill 7 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

Hotel Paradise (Dance Area!)

Rams Head On Stage 30 Nov 2025

Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

Rams Head On Stage 7 Dec 2025

Last Train Home

Rams Head On Stage 2 Jan 2026

Siren's Call

The Westin Annapolis 12 Dec 2025

Siren's Call

The Westin Annapolis 5 Dec 2025

Thanksgiving Karaoke - Powered by KJ DJ Ben

Caliente Grill 26 Nov 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Siren's Call

The Westin Annapolis 19 Dec 2025

Grand Illumination Tree Lighting - Downtown Annapolis 2025

Market Space, Annapolis, MD 21401, United States 30 Nov 2025

Jon McLaughlin & Friends: Home For The Holidays

Rams Head On Stage 21 Dec 2025

Siren's Call

The Westin Annapolis 26 Dec 2025

Laura Tsaggaris (Matinee)

Rams Head On Stage 6 Dec 2025

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 5 Dec 2025

Atlanta Rhythm Section at Rams Head On Stage

Rams Head On Stage 6 Dec 2025

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

Rams Head On Stage 13 Dec 2025

Chris Isaak

Maryland Hall For The Creative Arts 6 Dec 2025

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

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

Tab Benoit

Rams Head On Stage 6 Dec 2025

Tides & Tunes

The Westin Annapolis 2 Dec 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

Shakey Graves

Rams Head On Stage 13 Dec 2025

Jimmie's Chicken Shack Holidaze Show

Rams Head On Stage 26 Dec 2025

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

Rams Head On Stage 13 Dec 2025

U2topia: The Mid-Atlantic U2 Tribute Band

Rams Head On Stage 28 Nov 2025

Siren's Call

The Westin Annapolis 28 Nov 2025

The Gilmour Project: Wish You Were Here

Rams Head On Stage 9 Dec 2025

A SQRRL! Holiday (Matinee)

Rams Head On Stage 20 Dec 2025

Live Arts Maryland presents Bluegrass Nutcracker

Annapolis Mall 5 Dec 2025

Tides & Tunes

The Westin Annapolis 9 Dec 2025

Be Still and Know: A Journey Into Sound & Soul

Unity by the Bay 5 Dec 2025

Cash Unchained – The Ultimate Johnny Cash Tribute

Rams Head On Stage 22 Jan 2026

Midnight Madness: Author Signing & Irish Music

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 11 Dec 2025

A Colonial Yuletide

186 Prince George St, Annapolis, MD 21401-1724, United States 6 Dec 2025

The Chuck Brown Band (Dance Area!)

Rams Head On Stage 31 Jan 2026

Tides & Tunes

The Westin Annapolis 16 Dec 2025

Encore Chorale Annapolis - 12/6 Concert

Maryland Hall 6 Dec 2025

DMTB: The Dave Matthews Tribute Band: Tomorrow We Die Tour

Rams Head On Stage 25 Jan 2026

Rams Head Presents Chris Isaak - Annapolis, MD

Maryland Hall 7 Dec 2025

Danny Burns Band: Southern Sky Album Release Tour

Rams Head On Stage 22 Dec 2025

Spa Creek Jazz at 49 W Annapolis

49 West Coffeehouse, Winebar & Gallery 6 Dec 2025

Chris Isaak Live On Tour

Maryland Hall 7 Dec 2025

Tell Me Lies - The Fleetwood Mac Experience

Rams Head On Stage 8 Jan 2026

2025 Santa Speedo Run

O'Brien's Oyster Bar & Seafood Tavern 13 Dec 2025

Live Arts Maryland Presents Handel's Messiah

St. Anne's Parish 21 Dec 2025

Tides & Tunes

The Westin Annapolis 23 Dec 2025

Pressing Strings

Rams Head On Stage 28 Dec 2025

Jon McLaughlin at Rams Head On Stage

Rams Head On Stage 21 Dec 2025

Rams Head Presents The Bacon Brothers: Freestanding Tour - Maryland Hall - Annapolis, MD

Maryland Hall 22 Jan 2026

Peter Mayer: A Stars and Promises Christmas 2025

Rams Head On Stage 11 Dec 2025

Bay Winds Band - 2025 Holiday Concert

St. Martin's Lutheran School of Annapolis 7 Dec 2025

Bay Winds Band Holiday Winter Concert

Unity by the Bay (Maryland) 16 Dec 2025

Danny Burns Band

Rams Head On Stage 21 Dec 2025

Annapolis Contra Dance! With Contre Temps and caller Andrea Nettleton

Annapolis Friends Meeting, Quakers 29 Nov 2025

LIVE MUSIC with Rickshaw Lizard

Blackwall Hitch - Annapolis 29 Nov 2025

The Young Fables in Annapolis, MD

49 West Coffeehouse, Winebar & Gallery 20 Feb 2026

Kashmir - The Led Zeppelin Experience

Rams Head On Stage 9 Jan 2026

Encore ROCKS Annapolis - 12/1 Concert

Maryland Hall 1 Dec 2025

Lights Parade Dinner Cruise with Ken's Creative Kitchen

1 Dock St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025

Seth Mitchell Band w/ Brooke Bell - 2nd Tuesdays at 49 West 12.9.2025

49 West St, Annapolis, MD 21401-2420, United States 9 Dec 2025

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 28 Nov 2025

Ana Popovic: Dance To The Rhythm Tour (Matinee)

Rams Head On Stage 11 Jan 2026

LIVE MUSIC with Red Betty & The Ruckus

Blackwall Hitch - Annapolis 6 Dec 2025

A Peter White Christmas at Rams Head On Stage

Rams Head On Stage 4 Dec 2025

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

Danah Denice Band at Rams Head On Stage

Rams Head On Stage 16 Jan 2026

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 28 Nov 2025

The Dave Matthews Tribute Band

Rams Head On Stage 24 Jan 2026

Mindi Abair & Vincent Ingala

Rams Head On Stage 3 Dec 2025

LIVE MUSIC with Michael McHenry Tribe

Blackwall Hitch - Annapolis 5 Dec 2025

Noelle & Jeff Full Band!

Middleton Tavern 5 Dec 2025

Live Music with Mad Planet

Rams Head Roadhouse 28 Nov 2025

LIVE MUSIC with Rick & The Revolving Doors

Blackwall Hitch - Annapolis 13 Dec 2025

Scorpion Rose

Blackwall Hitch - Annapolis 20 Dec 2025

Hyland Brothers Live @ Galway Bay

Galway Bay Irish Restaurant and Pub 5 Dec 2025

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

Rams Head On Stage 15 Feb 2026

Bill Starks with Greg Hardin in Annapolis

49 West Coffeehouse, Winebar & Gallery 20 Jan 2026

Pure Prairie League at Rams Head On Stage

Rams Head On Stage 5 Dec 2025

The Slip Hippies - Night Before Thanksgiving Party

Blackwall Hitch - Annapolis 26 Nov 2025

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

Rams Head On Stage 4 Dec 2025

LIVE MUSIC with Moon Cherry

Blackwall Hitch - Annapolis 19 Dec 2025

Atlanta Rhythm Section

Rams Head On Stage 5 Dec 2025

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 12 Dec 2025

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 26 Dec 2025

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

Rams Head On Stage 14 Dec 2025

Son Little w/ Candi Jenkins

Rams Head On Stage 2 Dec 2025

Chris Isaak at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 7 Dec 2025

The Magic of Cinema - April 18, 2026

Maryland Hall 18 Apr 2026

Dan Tyminski Band at Rams Head On Stage

Rams Head On Stage 13 Feb 2026

Noelle & Jeff Full Band!

Middleton Tavern 2 Jan 2026