Happening Next in Chesapeake City
Upcoming Events in Chesapeake City
The Party of the Year: GATSBY
Chesapeake Inn Restaurant & Marina
21 Nov 2025
ENTERTAINMENT
USD 65 TO 175
Decade80 LIVE on The Deck!
605 Second Street, Chesapeake City, MD, United States, Maryland 21915
8 Nov 2025
MUSIC
Olivia Reynolds Band at Chesapeake City VFW
Chesapeake City VFW
29 Nov 2025
MUSIC
Bohemia River Boaters Lighted Boat Parade
Chesapeake City Bridge
6 Dec 2025
PARADES
The Everafter LIVE on The Deck!
605 Second Street, Chesapeake City, MD, United States, Maryland 21915
7 Nov 2025
MUSIC
The Chesapeake Inn
Chesapeake Inn Restaurant and Marina
9 Nov 2025
Vintner’s Table: Wine & Soup Pairing Experience - Legacy Club Event
237 Bohemia Manor Farm Ln
1 Nov 2025
USD 45
Just a Bit Outside @ Chesapeake Inn
Chesapeake Inn
19 Dec 2025
HOLIDAY
Chesapeake City VFW
Chesapeake City VFW
7 Nov 2025
COUNTRY-MUSIC-FESTIVALS
The Collapse: Aftermath, a Scenario Paintball Event
OXCC - Outdoor Xtreme Chesapeake City Paintball & Airsoft
6 Dec 2025
TRIPS-ADVENTURES
Santa at Sinking Springs
Sinking Springs Retreat Center, LLC
9 Nov 2025
CHRISTMAS
Chesapeake City VFW
Chesapeake City VFW
20 Dec 2025
COUNTRY-MUSIC-FESTIVALS
Just a Bit Outside @ Chesapeake Inn
Chesapeake Inn Restaurant and Marina
27 Feb 2026
Olivia Reynolds Band at Unwined on the Water
Unwined on the Water
20 Dec 2025
MUSIC
A Journey to OZ • Dec 27 & 28
Chesapeake Inn Restaurant & Marina
27 Dec 2025
HOLIDAY
USD 32 TO 53
Chesapeake City UMC Annual Christmas Bazaar
450 Third Street, Chesapeake City, MD, United States, Maryland 21915
22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS
New Years Eve Deck Party 2026 at Chesapeake Inn!
Chesapeake Inn Restaurant & Marina
31 Dec 2025
NEW-YEAR
USD 39
NYE Ballroom Bash 2026 at Chesapeake Inn!
Chesapeake Inn Restaurant & Marina
31 Dec 2025
NEW-YEAR
USD 154
Holiday Sip & Shop "Between The Vines"
237 Bohemia Manor Farm Ln
14 Dec 2025
MUSIC
USD 22
Thanksgiving At The Tank Room
237 Bohemia Manor Farm Ln
27 Nov 2025
THANKSGIVING
USD 34 TO 111
More things to do in Chesapeake City
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Chesapeake City Events