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.

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.

Registration Hours:
6:30 am to 9:00 am
Rides start at 7:00 am
(Special tandem starts at 8:00 am)
Ride ends promptly at 6:00 pm
Last sweep 5:00 pm

$25 until May 15, 2020
$30 May 16 until June 27, 2020
$40 Day of Ride
– Blind riders ride for FREE
– No Refunds
– Fee includes map, marked route, sag wagon
and five food stops
– Gift for the first 450 registered riders

Make checks payable to Chestertown Lions Charities, Inc.

Register online:




Register By Mail:

Click here for a mail-in registration form.

Walk-in Registration:
Walk-in registration will be available on the morning of the ride. To speed up the registration process, print a mail-in registration form and have it completed with payment in-hand at the time of registration.