STURGIS — Motorcycle racing remains at the heart of the Sturgis Motorcycle Rally, and the Jackpine Gypsies Motorcycle Club is keeping that tradition alive with a full slate of racing during Rally week.
Brett Winsell of the Jackpine Gypsies said during the daily news conference Saturday that racing has been part of the club, and the Sturgis Rally, from the very beginning. The club began racing in the Sturgis area in the 1930s and has continued that tradition ever since.
Winsell noted that the Jackpine Gypsies are believed to be the oldest continuously active motorcycle club in the world.
This year’s racing includes American Flat Track competition at the Jackpine Gypsies grounds, featuring some of the fastest motorcycle racers in the world. Winsell said the club’s unique short track creates close, high-energy racing where riders battle for position throughout the race.
“When you come watch short track, it’s kind of like going to an MMA fight,” Winsell said. “They have to get in, they have to bang bars.”
Rally week also includes professional hill climb competition; amateur flat track racing, the popular local Verticross competition and a pro-am hill climb later in the week.
Winsell said the events showcase not only world-class competitors but generations of local riders. Jackpine Gypsies racing can include everyone from young children just beginning to ride to competitors in their 70s.
For the club, the racing is about more than competition. It is about preserving a piece of Sturgis history while giving residents and Rally visitors another way to experience the motorcycle culture that helped create the Rally.
“We’re just people that love motorcycles,” Winsell said. “It’s mostly youth and old guys that love to still race.”
Jackpine Gypsies — 2026 Rally Racing Schedule
Date
Event
Time
Sat., Aug. 8
AFT Caterpillar Jackpine Gypsies Super TT
5 p.m
Mon., Aug. 10
Pro/Am Hill Climb
10 a.m.
Mon., Aug. 10
AFT Caterpillar Jackpine Gypsies Short Track
5 p.m.
Tues., Aug. 11
Gypsie Tour
9 a.m.
Tues., Aug. 11
Amateur Flat Track
5 p.m.
Wed., Aug. 12
Verta-X
7 p.m.
Fri., Aug. 14
Amateur Hill Climb
10 a.m.