Chesapeake City Seafood Festival

Chesapeake City 13 Sep 2025

Fall Classic

Chesapeake Inn Restaurant and Marina 6 Sep 2025

Melissa & Joe Gorga Comedy Night!

Chesapeake Inn Restaurant & Marina 2 Oct 2025

Schaefer’s Canal House

208 Bank St, Chesapeake City, MD 21915 13 Sep 2025

Crush the Chesapeake 5K

Chesapeake Inn 7 Sep 2025

9-11 Memorial Bridge Walk

215 Lock St, Chesapeake City, MD 11 Sep 2025

Annual Halloween Costume Party!

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

Birds Watch Party with Desean Jackson

Chesapeake Inn Restaurant & Marina 14 Sep 2025

The Company Live at Unwined on the Water

Unwined on the Water 12 Sep 2025

Del Soul Show Band at Schaefers Canal House

Lighthouse Bar at Schaefer's Canal House 18 Oct 2025

Katelyn Christine Performs

The Bayard House 13 Sep 2025

Cindee & Jimi back at the Chesapeake Inn!

Chesapeake Inn Restaurant and Marina 12 Sep 2025

Schaefer's Canal House

Schaefer's Restaurant & Canal Bar 26 Sep 2025

Olivia Reynolds at Chesapeake City VFW

VFW ChesapeakeCity 18 Oct 2025

BIRDS WATCH PARTY!

605 Second Street, Chesapeake City, MD, United States, Maryland 21915 14 Sep 2025

Chesapeake Inn

Chesapeake Inn 13 Sep 2025

Olivia Reynolds at Unwined on the Water

Unwined on the Water 10 Oct 2025

Unwined on the Water

Unwined on the Water 20 Sep 2025

Justin Taylor | Chesapeake City MD

Bayard House Restaurant 18 Oct 2025

Endless Legends

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