4nd Annual Chestertown (MD) Weekend (formerly, Kent County Spring Fling)

Friday, May 22, 2026 to Monday, May 25, 2026
Chestertown, MD, USA
Century, Half Century, Metric Century, Multisport, Recreational, Tour

Join the Baltimore Bicycling Club on Maryland’s scenic and peaceful Eastern Shore, Memorial Day Weekend. Home base for this Chestertown Weekend is Washington College, in the historic port city of Chestertown. Riders may choose from the 4-day/3-night (Friday to Monday) package, or 3-day/2-night (Friday to Sunday), or the 1-day option (Sunday only).

Package includes college dorm accommodations, all-you-can-eat meals, recreational group rides with Leaders every day, picturesque cycling routes from 10 to 100 miles on quiet roads, picinic lunch on Sunday, ice cream social, 2 nights of live music, dancing, trivia contest, socializing, bike mechanic, and much more.

Riders of all levels of ability and interest are welcome, and there are plenty of fun activities for non-cyclist companions. This is a RAIN-OR-SHINE event.

This cycling weekend coincides with the annual Tea Party Festival and Memorial Day events hosted by the colonial town of Chestertown, just a 10-min walk from the College. The Festival features live music, artisan crafts, local food and drink, craft beer festival, living history demonstrations, crazy-funny Raft Race on the Chester River, tea toss reenactment, and 10-mile and 5K running races.

Chestertown, MD is 75 miles from Baltimore, 78 miles from Washington, DC, 85 miles from Philadelphia, 170 miles from New York, and easily accessible via I-95.

The Baltimore Bicycling Club’s website is: https://www.baltobikeclub.org/
The direct link to the registration page is: https://organizations.hakuapp.com/sites/organization_sites/4312105d13cb51bfb415