Just weeks after telling Lakeland Connect he was excited to “go for real” at the Calgary Stampede, Dewberry’s Cruise Bensmiller has come away with one of the event’s top honours.

The fifth-generation chuckwagon driver was named the 2026 Orville Strandquist Memorial Top Rookie Driver, an award presented annually to the highest-performing rookie in the Calgary Stampede Rangeland Derby.

In his Stampede debut, Bensmiller posted the best 10-day aggregate time among all rookie drivers, finishing with a cumulative time of 12:16.32. His performance placed him seventh overall in one of the most competitive chuckwagon events in the world.

The award is named in honour of legendary Calgary Stampede chuckwagon driver Orville Strandquist and recognizes the rookie driver who performs best over the entire 10-day competition.

When Lakeland Connect spoke with Bensmiller before the Stampede, he described earning his spot in the Rangeland Derby as a dream come true.

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

That opportunity quickly turned into one of the biggest moments of his young career.

Bensmiller comes from one of chuckwagon racing’s best-known families. The Dewberry driver is the sport’s first fifth-generation competitor, following in the footsteps of his grandfather Buddy Bensmiller, uncles Kurt and Chance Bensmiller, and stepfather Vern Nolin, all accomplished drivers in their own right.

Ahead of the Stampede, four-time World Champion Kurt Bensmiller told Lakeland Connect he believed Cruise had earned the opportunity.

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

Those words proved prophetic.

By the end of the Stampede, Cruise had not only established himself among the circuit’s rising stars but had also earned one of the event’s most prestigious rookie honours.

For the Bensmiller family, it is another milestone in a racing legacy that now spans five generations.