Chestertown Weekend 2026

Despite the raindrops, smiles dominated the event. Thanks to the many cyclists who took part in the Baltimore Bicycle Club’s 42^nd annual Chestertown Weekend! Some cyclists rode all four days, not letting the precipitation slow them down.

As always, there is so much to do at Washington College and in Chestertown over Memorial Day weekend, that even rain couldn’t dampen our spirits. From Friday’s delicious dinner buffet, to the homemade ice cream and live music, cyclists had a great time from day one. On Saturday, some of us drove to the fascinating Massey Aerodrome for some wonderful aviation history and a pizza lunch provided by Larry and Linda Black. Saturday’s evening live music, as always, was a big hit for both dancers and listeners. Sunday’s picnic rides were rain-free and the pavilion at Worton Park was full of cyclists enjoying the delicious food and being together. Later, the annual crazy raft race on the Chester River brought more smiles. Sunday evening’s trivia contest was great fun and showcased the cyclists’ intellectual prowess.

It was a very relaxed weekend this year that included making new bike friends, socializing over long meals, exploring Kent County, and enjoying impromptu happy hours.

Thank you to the Chestertown committee for all of their excellent and hard work: Rob Keiser; Stacy Spivak; Adriana Pukalski, Linda McGrane; Frank Blatt; David Schallich; and Michael Reinsel. Thanks also to the excellent ride leaders who shepherded riders on the beautiful less-travelled lanes—especially Robbie Powell who joins us every year from St. Louis and shares his love of cycling with everyone. A shout out to Jon and Lisa from Atlanta, too!

This year many new cyclists joined the Chestertown Weekend family, and we hope they will join us again next year with friends in tow. Mark your calendars for the Chestertown Weekend 2027—May 28-May 31, 2027!           

Michael Reinsel