STURGIS, S.D. — Dirt-track motorcycle racing in Sturgis is not just a season; for many families and longtime club members it’s a lifelong way of life that stretches back to the first races held here in 1938.
Roots at the Jackpine Gypsies track
The Jackpine Gypsies Motorcycle Club staged the rally’s inaugural race at a worn-down half-mile track north of Interstate 90 in 1938. That same circuit continues to host riders nearly nine decades later, a physical link to the town’s racing heritage and a training ground for youngsters learning to navigate the shale and dust of flat-track and motocross.
Wiff Withey, an 83-year-old road captain for the Gypsies, has been mentoring young racers in motocross for more than 20 years. Withey says he knew “Pappy” Hoel — the club’s founder — and remembers racing Offenhauser engines with him at the Indianapolis 500. He stands near the hill climb at the club grounds greeting competitors from children on small-bore bikes up to adults in larger classes.
“It’s all about the kids,”
Withey said, underscoring why older riders and volunteers continue to invest time and labor in teaching the sport’s next generation. Though he stopped racing competitively at 59 after breaking his back, Withey still competes in vintage trial endurance events and attends club races to support younger riders.
From backyard tracks to national spotlight
For many South Dakota families, motocross and flat-track racing are year-round commitments. Parents build practice tracks behind cornfields, take paid time off work to travel to training camps and competitions, and maintain bikes between event weekends. That grassroots engagement fuels a pipeline of talent that occasionally reaches national stages.
This month the Jackpine Gypsies drew more than 4,000 fans under the lights for rally races, where Dallas Daniels, a 23-year-old Estenson Racing Yamaha professional, won both the Super TT and Short Track events — a “Sturgis double.” Daniels’ victories marked his first back-to-back national wins aside from Daytona and gave him momentum heading into the American Flat Track (AFT) grand nationals.
Season calendar and what’s next
Motorcycle racing season in the region runs through the fall. Two dates of particular interest to local competitors and fans:
- AFT nationals — Sept. 5–6 in Springfield, Illinois
- Local rally races — continuing through the fall at the Jackpine Gypsies grounds north of I‑90
Those planning to attend regional or national events should check schedules and entry requirements with organizers, and local riders often coordinate travel and lodging well in advance, given the communal nature of support crews and equipment transport.
Community and continuity
Club members emphasize that the sport’s survival depends on hands-on mentorship and family involvement. Older members know riders by name, tend to the bikes, and volunteer at events. Riders span the age and engine-size spectrum from tiny youth bikes to adult classes up to 600cc engines, often described in local parlance as “50 to 600ccs.”
For families who have made racing part of their identity, the return on those investments is not only trophies but a sense of belonging. The Jackpine Gypsies’ history and continued activity provide a stable setting where experience is passed down and where community members rally to keep the tracks active.
| Item | Detail |
|---|---|
| Club | Jackpine Gypsies Motorcycle Club |
| Original race | 1938 |
| Notable recent winner | Dallas Daniels (Super TT & Short Track) |
| Upcoming national event | AFT nationals, Sept. 5–6, Springfield, Illinois |
Practical notes for locals
People interested in getting involved can look for club race days at the Gypsies’ grounds north of I‑90, where volunteers typically handle registration and safety briefings. New riders often start on smaller-bore machines and participate in youth divisions before moving into higher-capacity classes. For spectators, events offer family-friendly viewing, food vendors and the chance to meet riders and crew.
As Withey and other longtime members make clear, the sport’s future in Sturgis depends on that intergenerational commitment — teaching checkered-flag skills on dusty tracks while keeping alive a piece of South Dakota’s motorcycling legacy.
