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 country stores. The 26 mile ride goes through historic Chestertown. Spend the day touring the town, then return to join your friends at the beach. Temperatures of late June lend themselves to a pleasant swim in the Chesapeake Bay at the end of the ride.