2026 Racing Season Overview
The 2026 racing season at OOYC features thirteen weeknight races broken into two Thursday night series along with three exciting trophy races for both spinnaker and genoa-only fleets.
Interested in crewing, racing your own boat, spectating, or serving as race committee? We would love to have you! Contact OOYC Fleet Captain, Darren Leonard for information at fleetcaptain@ooyc.org
Thursday Night Course Racing – June 11 to September 3, 2026
At Oak Orchard, Thursday nights signal the official start of the weekend! Racers, spectators, and race committee volunteers gather for an evening of engaging and spirited action on the water.
The Genoa Only fleet competes for the Ray Leonard Trophy, awarded to the season’s overall winner, while the Spinnaker fleet races for the prestigious Robert Muscarella Trophy.
Following the competition, all members and guests—whether coming in off the water or not—are invited to the clubhouse to enjoy food, drinks, and lively camaraderie, making Thursday nights a perfect blend of racing and community.
14th Annual Henri Cup Invitational – July 11, 2026
The Henri Cup Invitational, sponsored by the DeValk family, brings sailors together each summer to honor the memory of Henri DeValk, a guiding presence in OOYC’s history. This challenging 15 nm course invites crews from neighboring harbors to share in a race marked by tradition, friendly competition, and the simple pleasure of time on the water.
Following the race, join us for the new and improved Henri Cup party—now featuring a live band! It’s the perfect way to cap off the day with music, dancing, and a festive vibe that brings the racers, members, and guests together.
Fleets include Spinnaker, Genoa Only, and Double-Handed.
(Links: 2026 Henri Race documents: NoR • Flyer)
The Lakeside Race – August 8, 2026
The Lakeside Race returns in 2026, continuing a long-standing OOYC tradition. The race traces its roots to the year 1952, when it was first sailed as a regatta between Oak Orchard’s Snipe Fleet and the Lakeside Comet Fleet—a contest won by Francis Blake of OOYC. It was later revived in 1972 (and supported by Bunny White DeValk) as a handicap race for keelboats, run from Oak Orchard to Lakeside Beach and back, and was held annually through 1999.
After its reintroduction in 2024, the Lakeside Race now proudly enters its third consecutive year in this renewed era (and 34th running overall). The two-legged course sees competitors begin at a start line near the harbor to a mark off Lakeside Beach/Johnson’s Creek before returning homeward. Steeped in club history, the event offers not only a challenging and engaging sail but also the opportunity to compete for the race’s historic chamber pot trophy, a longstanding symbol of Lakeside tradition.
The Ketchup Race – September 5, 2026
A Labor Day weekend favorite and the ultimate highlight of the OOYC racing season! More than 45 years ago, Paul Drushler launched what may have been the first pursuit race on the Great Lakes, and the tradition lives on with thrilling action on the water.
Once the race is done, the party kicks into high gear! Join your party masters,Tim Quirk and Dana Leonard, for their second year hosting the legendary post-race bash. The afternoon features a live band pumping out tunes, Bloody Marys flowing freely, great food, raffles with exciting prizes, and non stop laughter, fun, and spirited revelry. No need to race to join the fun—everyone is welcome to celebrate, toast the season, and soak up the energy at OOYC!
OOYC Sailing Banquet – September 21, 2026
Join us for the 2026 OOYC Sailing Banquet, a celebration of a season well sailed! This casual afternoon brings together members, families, and friends to honor racing achievements and celebrate the camaraderie that makes OOYC special.
Enjoy a delicious steak roast dinner, lively conversation, and plenty of laughter as we reflect on the season’s highlights—from thrilling races on the water to memorable clubhouse moments. Whether you competed in the fleet, spectated from shoreside, or simply enjoyed the summer at the lake, this banquet is the perfect way to wrap up the season in style.
Dress is casual, the atmosphere is warm, and the night promises fun, recognition, and community spirit at Oak Orchard Yacht Club!