Jim Gent Memorial Bay 2 Bay Ride 2027

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 still-enjoyable, but 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.  

The registration fee includes:

1. access to RWGPS maps as well as printed map/cue sheets
2. a cool souvenir
3. a famously-well-marked route
4. SAG wagon
5. up to five food stops.

Registration Hours: 06:30 am until 09:00 am

The Ride starts at 0700 am - All routes begin & ends at the Betterton Volunteer Fire Company

Your registration gives you access to RWGPS maps.

Volunteers will direct you to parking upon arrival.