Annapolis Live Music Events

Live Music Happening Next in Annapolis, MD

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025
ART

Richard Thompson in Annapolis

St. John's College - Francis Scott Key Auditorium 2 Nov 2025
ENTERTAINMENT

Najee in Annapolis

Rams Head On Stage 9 Nov 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

2025 Hall & Friends Oyster Roast

Bay Ridge Marina 1 Nov 2025
MUSIC

Chris Isaak in Annapolis

Maryland Hall 7 Dec 2025
CONCERTS

Najee in Annapolis

Rams Head On Stage 9 Nov 2025
CONCERTS

Wishbone Ash: Wishlist Tour

Rams Head On Stage 8 Nov 2025
MUSIC

Keb' Mo' in Annapolis

Maryland Hall 21 Nov 2025
CONCERTS

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 7 Nov 2025
ENTERTAINMENT

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 2 Nov 2025
FESTIVALS

Annapolis Chocolate Binge Festival

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

Siren's Call

The Westin Annapolis 31 Oct 2025
MUSIC FREE

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
CONCERTS

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025
ART

Crack the Sky

Rams Head On Stage 1 Nov 2025
MUSIC

Will Hoge Band w/ July Moon

Rams Head On Stage 16 Nov 2025
MUSIC

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025
CONCERTS

Siren's Call

The Westin Annapolis 28 Nov 2025
MUSIC FREE

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025
ENTERTAINMENT

Dan Navarro w/ Jesse Lynn Madera

Rams Head On Stage 6 Nov 2025
ENTERTAINMENT

Siren's Call

The Westin Annapolis 5 Dec 2025
MUSIC FREE

Siren's Call

The Westin Annapolis 19 Dec 2025
MUSIC FREE

Signature Series: Darkness to Light

Maryland Hall for the Creative Arts 8 Nov 2025
ENTERTAINMENT

Macy Gray at Rams Head On Stage

Rams Head On Stage 2 Nov 2025
TRIPS-ADVENTURES

Siren's Call

The Westin Annapolis 26 Dec 2025
MUSIC FREE

Lights Parade Dinner Cruise with Ken's Creative Kitchen

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

Tides & Tunes

The Westin Annapolis 4 Nov 2025
MUSIC FREE

Marshall Crenshaw: 40+ Years in Showbiz

Rams Head On Stage 14 Nov 2025
MUSIC

Halloween Costume Party

2016 Industrial Dr, Annapolis, MD, United States, Maryland 21401 31 Oct 2025
COSTUME-PARTIES

The Moment Live Band & Show

1707 Forest Dr 1 Nov 2025
MUSIC USD 23

Laura Tsaggaris (Matinee)

Rams Head On Stage 6 Dec 2025
MUSIC

Tides & Tunes

The Westin Annapolis 11 Nov 2025
MUSIC FREE

Siren's Call

The Westin Annapolis 7 Nov 2025
MUSIC FREE

Keb Mo at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 21 Nov 2025
CONTESTS

Paapa-Berchie, Live Music Experience

Annapolis Mall 22 Nov 2025
MUSIC USD 34

The Brit Pack: British Invasion & More!

Rams Head On Stage 22 Nov 2025
MUSIC

Colin Hay in Annapolis

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

Acoustic Alchemy

Rams Head On Stage 12 Nov 2025
MUSIC

North Mississippi Allstars

Rams Head On Stage 7 Nov 2025

Tides & Tunes

The Westin Annapolis 18 Nov 2025
MUSIC FREE

Siren's Call

The Westin Annapolis 14 Nov 2025
MUSIC FREE

Naptown Flea

24 Market Space 9 Nov 2025
FLEA FREE

Navy Midshipmen Tailgate Party

The Westin Annapolis 15 Nov 2025
ENTERTAINMENT FREE

Will Hoge at Rams Head On Stage

Rams Head On Stage 16 Nov 2025
CALENDAR

Pure Prairie League at Rams Head On Stage

Rams Head On Stage 5 Dec 2025
CONTESTS

Siren's Call

The Westin Annapolis 21 Nov 2025
MUSIC FREE

Dan Navarro at Rams Head On Stage

Rams Head On Stage 6 Nov 2025
TRIPS-ADVENTURES

U2topia: The Mid-Atlantic U2 Tribute Band

Rams Head On Stage 28 Nov 2025
ENTERTAINMENT

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

Rams Head On Stage 13 Dec 2025
MUSIC

Sunday Fun Day & Art Walk in Downtown Annapolis

172 Green St 1 Nov 2025
ART USD 29 TO 50

Tab Benoit: I Hear Thunder Tour w/ Jesse Dayton

Rams Head On Stage 7 Dec 2025
MUSIC

Siren's Call

The Westin Annapolis 12 Dec 2025
MUSIC FREE

Marshall Crenshaw

Rams Head On Stage 13 Nov 2025
CONTESTS

The Jerry Douglas Band at Rams Head On Stage

Rams Head On Stage 5 Nov 2025
MUSIC

Natalie Merchant at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 23 Nov 2025
ART

Peter Mayer: A Stars and Promises Christmas 2025

Rams Head On Stage 11 Dec 2025
MUSIC

Wishbone Ash at Rams Head On Stage

Rams Head On Stage 8 Nov 2025

Tides & Tunes

The Westin Annapolis 16 Dec 2025
MUSIC FREE

Noelle & Jeff Full Band!

Middleton Tavern 7 Nov 2025
MUSIC

The Martin Sexton Abbey Road Show at Rams Head On Stage

Rams Head On Stage 21 Nov 2025
TRIPS-ADVENTURES

Annapolis Jazz & Roots - Ed Hrybyk "Bass Traditions"

Anne Arundel County Public Library (Eastport-Annapolis Neck Library) 15 Nov 2025
MUSIC

Carbon Leaf

Rams Head On Stage 12 Dec 2025
TRIPS-ADVENTURES

Rams Head Presents Chris Isaak - Annapolis, MD

Maryland Hall 7 Dec 2025
ENTERTAINMENT

Tides & Tunes

The Westin Annapolis 23 Dec 2025
MUSIC FREE

Uli Jon Roth at Rams Head On Stage

Rams Head On Stage 13 Nov 2025

Vienna Teng at Rams Head On Stage

Rams Head On Stage 20 Nov 2025

Uli Jon Roth

Rams Head On Stage 12 Nov 2025
TRIPS-ADVENTURES

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 31 Oct 2025
MUSIC

Cash Unchained – The Ultimate Johnny Cash Tribute

Rams Head On Stage 22 Jan 2026
MUSIC

Tides & Tunes

The Westin Annapolis 30 Dec 2025
MUSIC FREE

Wishbone Ash

Rams Head On Stage 7 Nov 2025
TRIPS-ADVENTURES

Candlelight: Tribute to The Beatles | Annapolis

Hubbard Hall (Annapolis, Maryland) 20 Nov 2025
CANDLELIGHT-CONCERTS

Taste of Fall on West Street

53 West St 9 Nov 2025
MUSIC USD 7 TO 82

Marshall Crenshaw at Rams Head On Stage

Rams Head On Stage 14 Nov 2025
TRIPS-ADVENTURES

Comic & Music Fair

ArtFarm 8 Nov 2025
FREE

Jim Messina and his band The Road Runners

Rams Head On Stage 25 Nov 2025
MUSIC

Scorpion Rose

Blackwall Hitch - Annapolis 20 Dec 2025
MUSIC

THE SAMPLES

Annapolis Smokehouse And Tavern 20 Nov 2025
USD 54

Tides & Tunes

The Westin Annapolis 25 Nov 2025
MUSIC FREE

Tides & Tunes

The Westin Annapolis 2 Dec 2025
MUSIC FREE

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025
CALENDAR

The Gilmour Project: Wish You Were Here

Rams Head On Stage 9 Dec 2025
MUSIC

Najee (7:30PM Show)

Rams Head On Stage 9 Nov 2025
MUSIC

Tides & Tunes

The Westin Annapolis 9 Dec 2025
MUSIC FREE

Son Little w/ Candi Jenkins

Rams Head On Stage 2 Dec 2025
MUSIC

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

Rams Head On Stage 14 Dec 2025
MUSIC

Chris Isaak at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 7 Dec 2025
CONTESTS

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 12 Dec 2025
TRIPS-ADVENTURES

Tab Benoit at Rams Head On Stage

Rams Head On Stage 7 Dec 2025
CONTESTS

Ana Popovic: Dance To The Rhythm Tour (Matinee)

Rams Head On Stage 11 Jan 2026
MUSIC

One Step Down at Rams Head Tavern in Annapolis, MD

Rams Head Tavern Annapolis 5 Dec 2025

Versed Fox

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 12 Nov 2025
ART