A few words come to mind when off-road three-wheelers are brought up in conversation, but "safe" is not one of them. You wouldn't think to take such a rig on a cross-country road trip, then, but that's probably because you aren't Matt Webb. He's trekking across Canada as we speak—in the winter—on a Honda Big Red, all in memory of a departed friend. He also hopes to set a Guinness World Record in the process.
"Twenty years ago, I worked for a guy and my first purchase after getting that paycheck was a Big Red 250," Webb told me over the phone. "I drove that thing back and forth to work for a year."
His boss told him he'd give him $1,500 if he could ride it to Nova Scotia. "I ended up selling it and regretted it ever since," Webb said. "I've been thinking about that trip the whole time."
The idea festered in his mind until 2022 when he decided it was finally time for the epic road trip. He started Jan. 1 in 100 Mile House, British Columbia, which is on the far west side of Canada; he'll hopefully end at Prince Edward Island, which is about as far east as you can go, save for the very tip of Newfoundland and Quebec. He's already amassed nearly 40,000 TikTok followers as people across Canada have invited him for a warm meal and the occasional place to stay.
Webb is riding through the snow, ice, and fog with a small trailer attached holding milk crates full of gear. The adventure has presented one trial after another for the past few weeks, though he's doing it for a reason.
"My friend Anthony passed last year and I basically worked myself to death, avoiding life and everything else," Webb explained. "I finally said, 'To hell with it, man. No better time than now.' I got this three-wheeler for $500 from a buddy and decided this was the one."
Webb made a call to Guinness to notify them of his attempt, stuck a sign on the back to avoid heat from cops, and has already covered more than 2,000 kilometers. He expects to eventually eclipse 10,000 kilometers total, or roughly 6,200 miles. That's more than most of us would dare to drive in an old car, let alone a 200cc trike that's restricted to ditches and dirt roads.
He was at Saskatchewan's western border with Alberta when we spoke late last week, and on Jan. 16, he had parked in Wolseley, nearly to the eastern border of the province, close to Manitoba. Webb isn't embarking on a speed run, though. He's strictly focused on distance.
"I'm not trying to do the fastest route from here to there; I'm trying to get the most kilometers. I'm zig-zagging up and down, through backroads. Honestly, how I've taken my route is looking at the map and picking a funny name or a name I can't pronounce, then finding the local watering holes, restaurants, and cheap hotels. No bed bugs yet," Webb joked.
The cops have left him alone up to this point, and should they pull him over, Webb has correspondence with Guinness to serve as some sort of proof for his record attempt. He's also accepting donations for Bikers Down Society, a charity that's focused on helping Canadian riders who were injured in motorcycle crashes. Every dollar is in memory of his friend Anthony, with Webb putting just 25% away for his own expenses.
"All this trip has come out of my own pocket, right? So 75% of the donations go to them and 25% goes to me," Webb said. "The long and short of it, every $100, I get an oil change."
It's tough to say how long it'll take Webb to reach Nova Scotia, especially if he's driving every way but west to get there. Rest assured, though, that it'll be a mighty journey when all is said and done. He's in it for the long haul, making friendships and raising money for a stellar cause along the way.
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