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 27 and 104 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 27 mile ride goes through historic Chestertown for those who want a less challenging ride. Spend the day touring the town, then return to join your friends just up the hill from Betterton Beach. Temperatures of mid-June lend themselves to a pleasant swim in the Chesapeake Bay at the end of the ride.