Happening Next in Chesapeake City
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
Baker’s Restaurant Presents Max & Denise “Acoustic With An Edge”
Baker's
15 Nov 2025
MUSIC
More things to do in Chesapeake City
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Chesapeake City Events