2021 Bay to Bay Ride Info

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 26 and 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 for those who want a less challenging ride.

If you’ve registered, y0u can find the route details here.

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.

Time:
Check-in Hours: 6:30 am to 9:00 am
Rides start at 7:00 am until 9:00 am
Ride ends promptly at 6:00 pm
Last sweep 5:00 pm

Cost:
$25 until May 15
$30 May 16 until June 15
$40 June 16 until Friday, June 25
– Blind riders ride for FREE.
– Fee includes map, marked route, sag wagon and five food stops.
– Masks must be worn at check-in and food stops.

Due to the Covid-19 measures, registration will be pre-registration only.

Make checks payable to Chestertown Lions Charities, Inc.

Register online:

  active_com

Register By Mail:

Click here for a mail-in registration form.

No walk-in registration:
Due to the Covid-19 measures, registration will be pre-registration only.

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