Kim Rocheleau is the founder of the Dirt Divas women's mountain biking group and successfully led 13 Women's 100 road cycling events in Windsor-Essex (PROVIDED BY K. ROCHELEAU/University of Windsor)
By Kate Hargreaves
When Kim Rocheleau (BHK ’95, BEd ’06) finishes her workday as a high school principal with the Greater Essex County District School Board, she often hits the road — or the trail — on two wheels rather than four.
When she’s not supporting students and staff at Vincent Massey Secondary School, she shares the joy of cycling with women across Essex County.
Earlier this month, she organized the 13th annual — and final — local Women’s 100, marking more than a decade of leading the inclusive cycling event.
While she may have wrapped up the Women’s 100, Rocheleau is still going strong when it comes to supporting women in cycling.
“I felt fulfilled and a bit emotional,” she recalls of this year’s event. “I was happy to end on such a positive high note and thrilled that so many women participated year after year.”
While the 2026 finale brought together more than 40 women to ride either 100 km or 100 minutes together, the event was much smaller when Rocheleau first introduced the Women’s 100 to Windsor in 2013.
She had heard that cycling apparel company Rapha had launched the Women’s 100, a global event that encourages women around the world to ride 100 km on the same day. In a sport often dominated by men, and where getting started can be intimidating, the event aimed to empower women to share the joy of road cycling.
Thirteen years later, Rocheleau has organized the Windsor-Essex Women’s 100 every year since, including a solo version during COVID-19 lockdowns, and has expanded the event from a single 100 km road ride to include a more accessible 100-minute ride.
On many of these occasions, the 100 km ride included women completing their first metric century, a major accomplishment. Rocheleau says it feels amazing to have helped facilitate these milestones.
"I’m empowered by these women and learn so much from them,” she says.
“It fuels my passion for cycling. I remember how so many others helped me along the way, and it’s gratifying to give back.”
Rocheleau’s own entry into cycling was also shaped by the people around her.
“I loved riding bikes growing up and especially on mountain bike trails,” Rocheleau recalls.
During her time as an HK student, she told her mother that she was interested in riding the kind of mountain bike trails she saw on television and in the Olympics.
Her mother had friends from work who shared the hobby and took Rocheleau mountain biking for the first time in Michigan.
"I absolutely loved it and was hooked,” Rocheleau says.
“This led into 24-hour team relays, adventure racing (navigating a run, paddle, mountain bike route), the Ontario Cup mountain bike race series, local races, Michigan race series, Xterra duathlons and eventually road racing and gravel racing.”
Well before launching the Women’s 100 locally, Rocheleau began sharing her love of off-road cycling, through her Dirt Divas women’s mountain biking group, which she has run for 23 years.
“Dirt Divas started as a result of many other women asking me to take them out on the trails,” Rocheleau explains.
“Rather than continuing to bring them out one at a time, I decided to invite them all out on a ride at the same time. It went really well, they continued to want to ride, and we eventually came up with the name.”
Dirt Divas has allowed Rocheleau to create a fun and welcoming environment for women to try the sport, meet others interested in cycling and build confidence together.
“It’s exciting to help others learn the sport, build skills and build fitness,” she says.
Empowering others through leadership is a principle Rocheleau brings to her day job as a principal.
While leading on and off the bike may seem vastly different, Rocheleau says there are similarities in how she approaches both roles.
“As a principal, I differentiate instruction and support to meet students and staff where they are at the time. In cycling, riders of different fitness and skill levels need to be monitored and encouraged,” Rocheleau explains.
Managing rider risk and safety also ties directly to her work in schools, where she must be prepared to respond to a crisis and maintain a safe environment. On the bike, that might mean coaching riders on safe riding, handling mechanical issues or watching for hazards.
“As a principal, I strive to build a welcoming and inclusive learning environment,” she adds, noting that she applies the same approach to leading rides.
“I’m building a welcoming and inclusive social environment where cyclists feel confident in their abilities and those around them.”
While the Women’s 100 may have wrapped up, Rocheleau continues to ride and lead the Dirt Divas while also planning to explore ways to share her love of bikepacking — travelling and camping by bike — with other women.
What keeps her rolling, she says, is the variety, the health benefits, the fun — and of course the people in the cycling community she continues to help build and support.
Those wishing to find out more about the Dirt Divas mountain bike group or get involved can follow @dirt.divas.mtb on Instagram.
This profile is part of a special series celebrating Alumni Week. Discover events and more at uwindsor.ca/alumni.
