Chesapeake City Music Events

The Party of the Year: GATSBY

Chesapeake Inn Restaurant & Marina 21 Nov 2025

Annual Halloween Costume Party!

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

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 18 Oct 2025

Nicks In Time @ Unwined on the water

Unwined on the Water 22 Nov 2025

MORE MORE MORE Band LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 3 Oct 2025

Baker’s Restaurant Presents Max & Denise “Acoustic With An Edge”

Baker's 15 Nov 2025

The Company LIVE on The Deck!

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

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

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

Gypsy Wisdom LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 18 Oct 2025

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 15 Nov 2025

The Collapse: Aftermath, a Scenario Paintball Event

OXCC - Outdoor Xtreme Chesapeake City Paintball & Airsoft 6 Dec 2025

Ken Miller Performing at Bayheads Brewing Company

Bayheads Brewing Company 24 Oct 2025

The Amigos @ Unwined on the Water

Unwined on the Water 18 Oct 2025

The Amigos @ Bakers Restaurant

Baker's 10 Oct 2025

Olivia Reynolds Band at Chesapeake City VFW

Chesapeake City VFW 29 Nov 2025

Jumper LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 24 Oct 2025

Del Soul Show Band at Schaefers Canal House

Lighthouse Bar at Schaefer's Canal House 18 Oct 2025

The Amigos @ Bakers Restaurant

Baker's 24 Oct 2025

THE EVERAFTER @ Chesapeake Inn

Chesapeake Inn 10 Oct 2025

The Chesapeake Inn

Chesapeake Inn Restaurant and Marina 9 Nov 2025

THE EVERAFTER @ Chesapeake Inn

Chesapeake Inn 13 Feb 2026

Joyride (The duo!) @ Chesapeake Inn, Chesapeake City, MD

Chesapeake Inn 2 Nov 2025

Chesapeake Inn Restaurant & Marina, Chesapeake City, MD

Chesapeake Inn 19 Oct 2025

UnWined on the Water

Unwined on the Water 29 Nov 2025

Olivia Reynolds Trio at Bakers

Baker's 1 Nov 2025

THE EVERAFTER @ Chesapeake Inn

Chesapeake Inn 7 Nov 2025