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Plan your trip early and stay in Chestertown! Click here for local lodging.

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Bay to Bay Jim Gent Memorial Ride

Ride starts/ends Betterton Volunteer Fire Company - 2 Howell Point Rd Betterton, MD 21610

The Chestertown Lions Club welcomes cyclists to the Bay to Bay ride. The tour consists of four routes 26, 50, 85, or 102 miles in length. The flat loop routes take in the scenery of the heartland of the Upper Eastern Shore of Maryland and Delaware including farmlands, old country homes, quaint towns, and great… Continue Reading Bay to Bay Jim Gent Memorial Ride

Halloween Parade

High Street , United States

The Chestertown Lions Club will host their annual Halloween Parade on Saturday, October 28th commencing at 1 pm in downtown Chestertown. This annual event has been delighting locals and visitors of all ages for over fifty years. The parade will proceed down High St beginning from Kent St. and ending at Queen St. The parade… Continue Reading Halloween Parade

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