calendar_today 27 Jun, 2026 – 28 Jun, 2026
directions_bike Cycling
language Official Website
sell $45.00 – $55.00
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.
Registration Hours 0630 am until 0900 am
Ride starts at 0700 am - begins & ends from the Betterton Volunteer Fire Department
Volunteers will direct you to parking upon arrival.
Jun 27, 2026
Distance — 164.2K
Type — Cycling
04:00
$55.00
Jun 27, 2026
Distance — 41.8K
Type — Cycling
04:00
$45.00
Jun 27, 2026
Distance — 80.5K
Type — Cycling
04:00
$55.00
Jun 27, 2026
Distance — 136.8K
Type — Cycling
04:00
$45.00
These values represent the 3-year monthly averages for June in Betterton.
Learn more about the host city, Betterton.
Betterton is a town in Kent County, Maryland, United States. As of the 2020 census, Betterton had a population of 286.
Read more launchRead what other athletes have to say about their experience at the Jim Gent Memorial Bay2Bay Ride - 2026.
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