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