Bike Trip Completed - Bay to Bay - Chesapeake Bay to Delaware Bay for Charity

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.

I, along with friends, have taken part in this ride 5 times between 2008 and 2018. Each time we ride the 103 mile 100% paved route which has 1,760 vertical feet of climbing at an average of 2.1% grade. The ride is characterized by rolling hills through fields of corn, wheat, soybeans, fruits and herbs, along with the occasional beef and dairy farm.

2021 Route for the 35th annual Bay to Bay Ride.

Ride elevation profile

When approaching the Delaware Bay you have to ride through the Woodland Beach State Wildlife Area. You enter the wildlife area when you cross Hay Point Landing Road. From this point it is a 3 mile race to the bay rest area and a 3 mile race back because it is in this area the dreaded Tabanus Nigrovittatus, also known as the greenhead horse fly lives. These ravenous creatures can fly fast and deliver a painful bite.