Manitoba Charity Ride Recap

Four Days. 500+ Kilometers. Headwinds and Sideways Rain. Zero Regrets.

This June, Brendan Willis, Ryan Archambault, Trevor Michalkow, and I (Tanya Wilson…support crew, emergency logistics lead, and morale officer) tackled our fourth leg in an ambitious cycling journey across Canada. This time: Manitoba. 

We made the trek in four days, from the Saskatchewan-Manitoba border to the Ontario signpost, through relentless headwinds, sideways rain, scattered thunderstorm warnings and a few moments of existential questioning. But we also saw big skies, rolling prairie views, and the quiet satisfaction that comes from pushing through hard things, together. All in support of youth and underserved communities through the Willis Family Foundation.

And yes, SpongeBob came along for the ride, courtesy of Trevor’s back jersey pocket, where he offered uninvited commentary, moral support, and emotional shade.

Day 1: 150 Kilometres and a Motel So Weird We Stopped Questioning It

We kicked things off with a three-hour drive to the Saskatchewan–Manitoba border, where the boys started their first 150 km leg into a steady 26 km/h headwind. Every possible lunch spot was closed, the mosquitoes had vendettas, and by kilometer 120, the boys were entering what can only be described as the absurd stage of fatigue. But despite all that, spirits stayed high, buoyed by blue skies, fresh legs (relatively speaking), and the unmistakable energy that comes with finally getting the wheels rolling. Manitoba was officially underway.

We finished the day in Minnedosa, where the motel’s front door and check-in counter doubled as a fried chicken franchise, and the rooms opened onto a vast indoor Astroturf courtyard complete with chandeliers. It was surreal, slightly absurd, and exactly the kind of energy Day 1 deserved.

**Click on the video thumbnail below to watch our quick Day 1 recap video.

Day 2: Flats, Pizza Socks & SpongeBob’s Debut

The day began in Minnedosa and stretched through long, windy farmland as the group cycled deeper into rural Manitoba. Early stiffness and tight legs were met with cool temperatures and deceptively open skies. The goal: reach Portage la Prairie by day’s end. 

A planned lunch stop at a roadside diner turned into a logistical hurdle when Brendan discovered he had blown a tire. It was a worst-case timing scenario as the group had already burned through most of their tube supply getting setup the previous day and this left them with only one remaining spare. Their remaining kilometers were powered almost entirely by legs, lungs, and blind faith in rubber.

Meanwhile, SpongeBob, who was tucked into Trevor’s jersey pocket, made his first official appearance on the ride. His deadpan stare quickly became the group’s unofficial mascot and occasional voice of judgement. He did not handle the crosswinds well.

By mid-afternoon, the team arrived in Portage la Prairie with just enough time to regroup, rehydrate, and scavenge for replacement tire tubes (successfully). Spirits lifted and morale officially rebounded with a hot tub soak that bordered on therapeutic.

Day 3: Tire Blowouts, Prairie Punishment & the Perogy Burger Redemption

Day 3 was 137 km of smoky, headwind-soaked character development. And by “character development,” I mean mild personality breakdowns and a lot of swearing into the prairie wind. The punishing gusts topped 48 km/h, with a brief tailwind that lasted approximately four minutes …just long enough to offer hope before cruelly snatching it away. Still, the team kept pushing with quiet determination and just enough laughter to hold off the full unraveling.

Things escalated just outside Winnipeg when Ryan blew a tire mid-ride, prompting a three-man roadside repair. Thankfully, we’d restocked our tube supply the night before, but the group was still visibly haunted by recent memories of running dangerously low. SpongeBob didn’t say much, but his judgement was palpable.

The team reached the geographic centre of Canada, where Brendan celebrated cycling halfway across the country.

Later that evening, spirits were revived with perogy burgers and beers in a small-town motel with slot machines in the bar and no check-in desk…just a bartender who sold room keys and cold cases.

Day 4: Thunderstorms, Freight Trains & and a Champagne Finish

Day 4 began with a 5:00 AM freight train that rattled both the motel walls and whatever optimism was left in the tank. It wasn’t so much an alarm clock as a full-body existential jolt. The in-room coffee came courtesy of a tea-bag-style pod and was brewed into a cup roughly the size of a contact lens case. Breakfast was leftover cold pizza. It was… not better the next day.

By 6:30AM, the boys were back on the bikes, sore, quiet, and facing 137 km between them and the Ontario border, plus a firm 7:00 PM reservation at Hy’s in Winnipeg, which had somehow become the emotional finish line. The forecast was grim. Brendan described the wind as “right in the teeth.”  Still, there was a sense of momentum that morning.  The kind that comes from knowing the finish line (and a perfectly grilled steak) is finally within reach.

A severe thunderstorm warning (complete with toonie-sized hail, lightening and heavy rainfall) came in just as I handed out their lunch orders at the first pit stop. By kilometre 40, the rain had begun. By kilometre 120, it was biblical. They ended the ride just shy of the Ontario border for safety, but still ran through puddles to grab the soggy finish line photo.

We closed the chapter with a bottle of champagne (a little surprise sent by Ryan’s wife Lisa) and dinner at Hy’s, where Ryan declared his Chicago Rare steak “the best he’s had in seven years.”

**Click on the video thumbnail below to watch our very wet Ontario signpost excursion.

Bonus: A Visit to the Mothership

The next day, we were hosted by Wellington-Altus head office for a post-ride hot dog lunch celebration and tour. Still a little road-worn, we were welcomed with open arms, warm congratulations, and just the right amount of “you did what?” disbelief.

It was exactly the kind of moment that makes us proud to be part of a firm that celebrates its people, backs big ideas, and applauds community involvement just as much as performance metrics.

Support the Cause

We rode for more than just the challenge. We rode to raise funds for youth programs and underserved communities through the Willis Family Foundation.

If you’d still like to support the cause, DONATE HERE.

Next year, we take on Ontario. Heaven help us.

Thanks for reading, supporting, and cheering from the sidelines.