Upcoming Events in Chesapeake City

Melissa & Joe Gorga Comedy Night!

Chesapeake Inn Restaurant & Marina 2 Oct 2025
COMEDY USD 54 TO 102

The Party of the Year: GATSBY

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

Cigars, Cards and Cocktails

318 Lindsey Ave 11 Oct 2025
SPORTS USD 29 TO 55

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
SPORTS

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
COSTUME-PARTIES

Harvest Festival at Cook Family Farms

3300 Frazer Rd, Newark, DE 4 Oct 2025
FESTIVALS

Stomp Box @ Chesapeake City VFW 7-11pm

Chesapeake City VFW 25 Oct 2025

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 18 Oct 2025
MUSIC

Chesapeake City Little League - Home Run Derby Fundraiser

Luff Lane 5 Oct 2025
NONPROFIT USD 34 TO 215

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
MUSIC

Joyride Halloween Party @ Baker's, Elkton, MD

Baker's 31 Oct 2025
HALLOWEEN

Simon at the Chesapeake Inn...

Chesapeake Inn 9 Oct 2025
NONPROFIT

Lost In Paris LIVE on The Deck!

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

Jackson Cole LIVE on The Deck!

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

MORE MORE MORE Band LIVE on The Deck!

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

More things to do in Chesapeake City