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Concerts this month in Chestertown, MD
Find tickets to concerts, tour dates and live music near Chestertown, MD
Chestertown, MD
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All Genres
Alternative
Blues
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Troll Tribe
Fri, Oct 2 • 3:30 PM
The Admirals Cup Annapolis
Samantha Seider
Fri, Oct 2 • 4:00 PM
Looney's Pub
Patrick Kozub
Fri, Oct 2 • 5:00 PM
Soul Sessions – Songwriter Circle
MIGGS
Fri, Oct 2 • 6:00 PM
MIGGS | The Backyard (Lonestar Acoustic)
Nelly's Echo
Fri, Oct 2 • 6:00 PM
Nelly's Echo at Jimmy's Famous Seafood
Jennifer Stella
Fri, Oct 2 • 6:00 PM
Big Truck Farm Brewery
Chris Montcalmo
Fri, Oct 2 • 6:00 PM
Jerry D's Saloon
The Funsters
Fri, Oct 2 • 6:00 PM
Annual Oktoberfest Festival and Benefit
Fitzkee Brothers Music
Fri, Oct 2 • 6:00 PM
Maritime Magic 2026
Milton J
Fri, Oct 2 • 6:30 PM
The Recher
Dave Zelonka
Fri, Oct 2 • 6:30 PM
Dave Zelonka Band @ Elkridge Assembly Rooms
SLOT
Fri, Oct 2 • 7:00 PM
Metro Baltimore
Freke Umoh
Fri, Oct 2 • 7:00 PM
Breath Of God: Worship Night with Freke Umoh
DJ Jamaal
Fri, Oct 2 • 7:00 PM
STK Baltimore
Margo Price
Fri, Oct 2 • 7:00 PM
Rams Head On Stage
Powerplant
Fri, Oct 2 • 7:00 PM
Metro Gallery
Skribe
Fri, Oct 2 • 7:00 PM
BRIAN BORU
Madisun Bailey
Fri, Oct 2 • 7:00 PM
Langways
Nikki Glaspie Fan Page
Fri, Oct 2 • 7:00 PM
Maritime Magic with Super Sonic Shorties
John Haywood
Fri, Oct 2 • 7:00 PM
Union Jack's Columbia
Applied Knowledge
Fri, Oct 2 • 7:00 PM
Holy Frijoles
AK7
Fri, Oct 2 • 7:00 PM
La Tolteca
Mike Masse
Fri, Oct 2 • 7:30 PM
Cultural Center at the Opera House
Ray Wroten
Fri, Oct 2 • 7:30 PM
Killarney House
Michael Longfellow
Fri, Oct 2 • 7:30 PM
The Port Comedy Club
DJ Aktive
Fri, Oct 2 • 8:00 PM
Docklands Riverfront
Fast Eddie & The Slowpokes
Fri, Oct 2 • 8:00 PM
New Deal Cafe
Loudon Wainwright III
Fri, Oct 2 • 8:00 PM
The Queen
Logan Ledger
Fri, Oct 2 • 8:00 PM
Rams Head On Stage
Glamour Kitty
Fri, Oct 2 • 8:00 PM
BareBones Grill in Ellicott City, MD
Lucy Kaplansky
Fri, Oct 2 • 8:00 PM
Kennett Flash
Young Gunz
Fri, Oct 2 • 8:00 PM
Docklands Riverfront
It's a 2000's Party
Fri, Oct 2 • 9:00 PM
It's A 2000's Party: Wilmington
Sirius Company
Fri, Oct 2 • 9:00 PM
HOUSE OF SOUL RESTAURANT and BAR
Sky City Social
Fri, Oct 2 • 10:00 PM
Catherine Rooney's
YOYOKA
Sat, Oct 3 • 12:30 AM
Jack Black Band (at Power To The People 2026) [SOLD OUT]
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