Melissa & Joe Gorga Comedy Night!

Chesapeake Inn Restaurant & Marina 2 Oct 2025

The Party of the Year: GATSBY

Chesapeake Inn Restaurant & Marina 21 Nov 2025

Cigars, Cards and Cocktails

318 Lindsey Ave 11 Oct 2025

Olivia Reynolds at Chesapeake City VFW

VFW ChesapeakeCity 18 Oct 2025

Endless Legends

2941 Old Telegraph Rd, , Chesapeake City, MD, United States, Maryland 21915 10 Oct 2025

Uncle Jesse LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 17 Oct 2025

Annual Halloween Costume Party!

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

Harvest Festival at Cook Family Farms

3300 Frazer Rd, Newark, DE 4 Oct 2025

Stomp Box @ Chesapeake City VFW 7-11pm

Chesapeake City VFW 25 Oct 2025

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 18 Oct 2025

Chesapeake City Little League - Home Run Derby Fundraiser

Luff Lane 5 Oct 2025

YARD SALE - SOUP SALE

351 Biddle St, Chesapeake City, MD, United States, Maryland 21915 4 Oct 2025

Olivia Reynolds at Unwined on the Water

Unwined on the Water 10 Oct 2025

Nicks In Time @ Unwined on the water

Unwined on the Water 22 Nov 2025

Joyride Halloween Party @ Baker's, Elkton, MD

Baker's 31 Oct 2025

Simon at the Chesapeake Inn...

Chesapeake Inn 9 Oct 2025

Lost In Paris LIVE on The Deck!

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

Jackson Cole LIVE on The Deck!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 11 Oct 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