Chesapeake City Live Music Events

Live Music Happening Next in Chesapeake City, MD

The Party of the Year: GATSBY

Chesapeake Inn Restaurant & Marina 21 Nov 2025
ENTERTAINMENT USD 65 TO 175

Annual Halloween Costume Party!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 25 Oct 2025
COSTUME-PARTIES

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 18 Oct 2025
MUSIC

Nicks In Time @ Unwined on the water

Unwined on the Water 22 Nov 2025
MUSIC

Lost In Paris LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 11 Oct 2025
LIVE-MUSIC

The Company LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 10 Oct 2025
MUSIC

Crab Fest Volunteer Fire Company #1 of Chesapeake City Inc.

215 Lock St, Chesapeake City, MD, United States, Maryland 21915 18 Oct 2025
MUSIC

Ken Miller Performing at Bayheads Brewing Company

Bayheads Brewing Company 24 Oct 2025
ENTERTAINMENT

The Amigos @ Unwined on the Water

Unwined on the Water 18 Oct 2025
MUSIC

The Amigos @ Bakers Restaurant

Baker's 10 Oct 2025
MUSIC

The Amigos @ Bakers Restaurant

Baker's 24 Oct 2025
MUSIC

Chesapeake City VFW

Chesapeake City VFW 7 Nov 2025
COUNTRY-MUSIC-FESTIVALS

THE EVERAFTER @ Chesapeake Inn

Chesapeake Inn 10 Oct 2025

UnWined on the Water

Unwined on the Water 29 Nov 2025
THANKSGIVING