What are the top concert venues in Chestertown, MD?

Chestertown, MD is home to iconic venues, including stadiums, amphitheaters, arenas, and intimate stages. Browse upcoming concerts and events at the following venues: Tolchester Marina Inc, shanty bar, Mainstay, Holden’s Chapel, Signals Restaurant and Deck Bar.

Upcoming Country Concerts & Events in Chestertown, MD

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Concerts in Chestertown, MD > Country

Country Concerts & Shows in Chestertown, MD

Know what you like? Discover upcoming country concerts and shows in Chestertown, MD. From legendary country artists to emerging local talent, explore artists in your preferred genre, and check out their upcoming concerts near you. Stay updated on the latest Chestertown, MD live music events and browse additional concert dates by genre, artist, and more.

Downtown Smyrna - Smryna, DE

Jun 20, 2026

THE ANNAPOLIS OPRY w The Black Eyed Suzies

St Margarets Episcopal Church

Apr 12, 2026

MIGGS | Red Eye's Dock Bar

Annapolis Baygrass Festival 2026

Sandy Point State Park

Sep 19, 2026

Vertigo Red @ Tolchester Marina

Tolchester Marina Inc

Jul 03, 2026

A Tribute to the Piano Men: Jerry Lee, Elton, Joel and More….

Julianne Jam with Jimmy Charles at Red Eye Dock Bar

Red Eye's Dock Bar

May 07, 2026

The Dirty Grass Players

Cult Classic Brewing

Apr 03, 2026

Annapolis Baygrass Festival 2026

Sandy Point State Park

Sep 19, 2026

Annapolis Baygrass Festival 2026

Sandy Point State Park

Sep 19, 2026

Alan Turner

The Smyrna Opera House

Oct 24, 2026

Larry Stephenson Band

Chesapeake Manor Vineyard & Winery

The Island at Flying Point Marina

Jun 18, 2026

Shake The Room Live!

The Island at Flying Point Marina

Ernie Couch & Revival

Back River United Methodist Church

Sep 11, 2026

The Wafflers Trio at Carson's Creekside

Carson's Creekside Restaurant & Lounge

Mar 28, 2026

Annapolis Baygrass Festival 2026

Sandy Point State Park

Sep 19, 2026

Harmony Woods Music Fest 2026

Maryland Center for the Arts

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Frequently Asked Questions About Chestertown, MD

Which artists are currently touring this city?

You'll find a variety of artists with Chestertown, MD tour dates. Follow your favorite artists or explore new ones; a few notable performers touring nearby include Vertigo Red, Rob Benton, and Josh Christina.

How many upcoming concerts are there happening in Chestertown, MD?

Currently, 33 upcoming events are scheduled in Chestertown, MD Browse tour dates and buy concert tickets to a show near you with Hypebot.