Difficulty: Moderate (some rolling steep hills)
On the fourth Sunday of June each year, the Chestertown Lions Club welcomes cyclists to its summer bicycling challenge, the Bay to Bay ride. The tour consists of five routes between 26 and 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 country stores. The 26-mile ride goes through historic Chestertown for those who want a less challenging ride.