Chesapeake City Live Music Events

Dueling Pianos with The Philly Keys

Chesapeake Inn Restaurant & Marina 17 Jan 2026

Bridgerton Ball!

Sinking Springs Retreat Center, LLC 21 Feb 2026

Triple Rail Turn LIVE on The Deck

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 7 Feb 2026

KONO Nation LIVE on The Deck

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 17 Jan 2026

Jackson Station band Jan.17 @VFW CHESAPEAKE CITY 7-11

VFW ChesapeakeCity 17 Jan 2026

The Amigos @ Bakers

Baker's 24 Jan 2026

Dueling Pianos with The Philly Keys • February 21

Chesapeake Inn Restaurant & Marina 21 Feb 2026

Dueling Pianos with The Philly Keys • February 20

Chesapeake Inn Restaurant & Marina 20 Feb 2026

The Amigos at Baker's Restaurant

Baker's 28 Feb 2026

Boy Band Brunch with The Boy Band Project

Chesapeake Inn Restaurant & Marina 19 Apr 2026

Vertigo Breeze Rockin the Chesapeake Inn

Chesapeake Inn 15 Feb 2026