Young and strapped for cash? Hop on a prewar bike to cruise America—for free

Kyle Smith

Whatever your automotive or motorcycle interest, there is always someone who is just a little bit crazier than you. For most of us that person is the one who keeps us engaged in the hobby. Watching their projects and pursuits inspires us to embark upon our own mechanical shenanigans. The trouble in this scenario is that such mentor figures typically have resources—shops, garages, lifts, cash—that younger enthusiasts simply don’t. Jason Sims, Alex Trepanier, and Cris Tribbey are on a quest to advocate for youngsters in just such a position. Sims has curated multiple events that any two-wheel fanatic would long to join, and Trepanier and Tribbey have joined him to create a path for younger enthusiasts to get on a bike and join motorcycle veterans in a cross-country road trip.

Sims is the man behind two different events that pit vintage motorcycles and their riders against the open road and each other. Grand tours that span coast to coast, or, in the case of the Cross Country Chase this year, border to center. The Motorcycle Cannonball is a 3000-mile odyssey designed for motorcycles over 100 years old—and riders who are willing to tackle a serious challenge.

pre-war motorcycle cannonball front wheel maintenance
Kyle Smith

As awesome as those treks sound, they are not cheap. Most enthusiasts who dabble in prewar motorcycles know that the high-mileage, big-event fun generally carries an equally hefty price tag. This inevitably creates a barrier to entry, one that many young folks who want to participate cannot surpass. Excluding young enthusiasts is a sure method to ensure an event’s eventual demise.

“Getting young people involved was something many participants had been talking about for three to four years,” says Sims. “Then Alex [Trepanier] put up a Facebook post, and it really started something.”

Alex Trepanier 46 indian FB post
Kyle Smith

What Trepanier did was a bold move. He wanted to put his money where his mouth was, so he volunteered his 1946 Indian for a young person to ride in the Motorcycle Chase event. “I am focused on Cannonball and realized I am lucky enough to have a bike or two that would be perfect for the Chase—but I don’t have the time to ride it.” Of course, with an offer like that, things start to happen fast.

Sims pointed out in our conversation that the bike is just one part of the equation. Chris Tribbey, a veteran of Cannonball, understands that fact as well as anyone. That is why he decided to back up Trepanier’s offer with a monetary contribution. Quickly other riders began adding to the cash pool, and this became a fund that would cover to the rider’s expenses for the journey. Tribbey and Trepanier made the decision to make the process democratic as well: Those who contributed would have the opportunity to vote in the process of selecting the lucky young rider.

“We decided on an essay contest to allow potential participants the opportunity to tell us about themselves. The people who applied did not make it easy to choose, either. There were so many good folks that took the time to let us know they were really interested,” says Trepanier. “When all the applications were in, there was three real standouts and it really pained us to pick just one.”

Luckily, they didn’t have to pick just one. Shortly after the group chose one fortunate rider for the ’46 Indian, two additional bikes became available, and the fundraising effort was reignited—this time, to cover two more riders’ expenses. It all happened quite fast–almost entirely during the one-hour livestream where they announced the first winner. Everyone involved is excited to see how an experience like this can ignite a lifelong love of motorcycles and adventure.

Sims’ focus when coordinating both the Cannonball and the Chase is the quality of riding. He’s not concerned with difficulty for difficulty’s sake, so he allows bikes with some mild modifications made in the interest of safety and reliability. Upgraded brakes—1970s Honda parts are popular—are nearly a must-have, along with modern tires. Running gear up-fitting, however, is restricted to keep the motorcycles true to their original identities. You won’t find a modern Mikuni carb at Sims’ events. A few 21st century riders might be joining the crowd, but their bikes will be the genuine, old-school article.

Trepanier and Tribbey hope, however, that the grand scheme will be far larger than three riders—or even a single event, like Cannonball. “We want to be able to send young folks to other events and schools, or programs to help keep this hobby and the bikes we love alive,” Trepanier said. “There are a lot of young folks who care, we just have to connect them and I think this shows that is possible.”

pre-war motorcycle cannonball gloves over engine
Kyle Smith

Due to the COVID-19 pandemic, the 2020 Cannonball and Chase events were postponed. Sims, Trepanier, and Tribbey know all the riders are looking forward to hitting the road this year—three young ones, especially. The crowd-sourced funding concept has gained enough traction that there is discussion and plans to set up a nonprofit endowment to expand the opportunity beyond a one-time offer, offering a seat to as many young enthusiasts as possible.

We’ll be keeping our ears tuned to the sound of a prewar cavalcade this September as the Cannonball heads south from Sault Ste. Marie, Michigan—there will be some new faces among the riders, and we can’t wait to meet them.

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