Most families have traditions.

The Bensmillers have chuckwagon racing.

For generations, the family has been a fixture on racetracks across Western Canada. From hauling horses and helping in camp to competing for championships, chuckwagon racing has become part of the family’s identity.

This summer, that story reaches another milestone.

Cruise Bensmiller is set to become chuckwagon racing’s first fifth-generation driver to compete in the Calgary Stampede Rangeland Derby, joining a family that has spent decades helping shape one of Western Canada’s most iconic sports.

“It’s definitely a family sport,” Cruise said while racing at the Bonnyville Chuckwagon Championship. “I’m here with my uncles, Kurt and Chance, and my stepfather, Vern Nolin.”

For most young drivers, earning a spot at the Calgary Stampede is a dream.

For the Bensmillers, it’s also a family affair.

Raised Around Horses and Wagons

Growing up in Dewberry, Cruise was surrounded by some of the biggest names in chuckwagon racing.

His grandfather is Buddy Bensmiller. His uncles are Kurt and Chance Bensmiller. His stepfather is Vern Nolin.

Together, they have won championships across both the WPCA and CPCA circuits and helped build one of the most recognizable family names in the sport.

But family history only gets you so far.

After making his driving debut in 2020, Cruise has steadily worked his way through the ranks. His breakthrough 2025 season included 15 top-ten runs, a berth in the Battle of the Foothills Championship Final Heat and his first career top-ten finish in the WPCA World Standings.

Now he is preparing for the biggest opportunity of his young career.

“Last year I got the demo, so I didn’t actually get to perform with everybody,” Cruise said. “This year, I actually get to go for real.”

A Proud Uncle Watching from the Track

Few people understand what that accomplishment means better than Kurt Bensmiller.

The fourth-generation driver has built one of the most impressive careers in modern chuckwagon racing, capturing four World Championships, four Calgary Stampede Rangeland Derby titles and a long list of other major championships.

But when the conversation turns to Cruise, the focus shifts from racing to family.

“It was a big deal,” Kurt said of Cruise qualifying for the Calgary Stampede. “Cruise is a great kid. Obviously, he was raised over a couple miles from our house because everybody’s pretty close, so we’re all invested in each other.”

Kurt believes Cruise has earned every bit of the opportunity.

“I think he should’ve been there a couple of years ago, for sure,” he said. “But yeah, he’s really progressed in the sport and seems to have a real handle on it early on.”

Photo Credit: Shelly Scott
Kurt Bensmiller Bonnyville 2026 Day 1 Fastest Time

More Than a Competition

For all the championships, trophies and prize money, both drivers say the family connections are what make the sport special.

“There’s not many jobs you can have where you literally live with your family for four months or six months out of the year,” Cruise said.

The racing season means long days on the road, countless hours around horses and plenty of time spent together between events.

It also means lining up against family members on the track.

“If I’m going to get beat, I’d probably want to get beat by my uncles,” Cruise said with a laugh.

A Lakeland Family Story

Around Dewberry and throughout the Lakeland, the Bensmiller name has become part of the chuckwagon landscape.

One generation taught the next, who taught the next, and now Cruise is carrying that tradition onto one of the biggest stages in the sport.

Kurt remains a contender. Chance continues to compete successfully across the circuit. Vern remains one of the most respected drivers in chuckwagon racing.

Now the fifth generation is stepping into the spotlight.

For the Bensmillers, it’s another summer at the track.

For chuckwagon racing fans, it’s a chance to watch a family tradition continue in real time.