Chesapeake City Live Music Events

The Party of the Year: GATSBY

Chesapeake Inn Restaurant & Marina 13 Nov 2026

BOH-jolais: A Harvest Wine Dinner

237 Bohemia Manor Farm Ln 19 Nov 2026

Decade80 at the Chesapeake Inn

605 Second Street, Chesapeake City, Maryland 21915 4 Dec 2026

Common Man Project LIVE on The Deck

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 21 Nov 2026

Under The Covers LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 14 Nov 2026

JUMPER LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 20 Nov 2026

Triple Rail Turn LIVE on The Deck

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 28 Nov 2026

UTC at Chesapeake Inn (Sat 11/14 7PM)

Chesapeake Inn Restaurant and Marina 14 Nov 2026

Chasing Red LIVE on The Deck

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 27 Nov 2026

Lion's Club Chesapeake City Christmas Tree Lighting

Pell Gardens Park 29 Nov 2026

Johnny Seaton Blue Christmas

208 Bank Street, Chesapeake City, MD, United States, Maryland 21915 13 Dec 2026

Chris & Dave at Baker's

Baker's 20 Nov 2026

Guys and Dolls Night @ Baker's

Bakers Restaurant & Cocktail Lounge 5 Dec 2026