Jim Gent Memorial Bay2Bay Ride - 2026

Jim Gent Memorial Bay2Bay Ride - 2026

The Chestertown Lions Club welcomes cyclists to our annual Bay to Bay Ride; this bicycling challenge offers four tours between 26 and 102 miles. The 50, 85, or 102 mile flat loop rides take in the scenery of the heartland of the Upper Eastern Shore of Maryland and Deleware including farmlands, old country homes, quaint towns and great country stores. For those who want a less challenging ride - the 26 mile ride goes through Historic Chestertown. Spend the day touring the town then return to join your friends at the beach. Temperatures in late June lend themselves to a pleasant swim in the Chesapeake Bay at the end of the ride. Fee includes map, marked route, SAG wagon and five food stops.

Event details and schedule

• Registration Hours: 06:30 am until 09:00 am
• Ride starts: 07:00 am - begins & ends from the Betterton Volunteer Fire Department
• Volunteers will direct you to parking upon arrival.