Waterloo trek looks to raise awareness and funds to tackle homelessness

Register now for The Crossing Trek and prepare to be inspired

People can make a difference, just ask Waterloo resident Tessa Jennison. And when people can make a difference doing what they love, which is the case with The Crossing Trek running on Feb. 8 in Waterloo, it’s even better. 

It was in the winter of 2018, frigid temperatures gripped Waterloo and Jennison was reading an article about local homeless shelters being over capacity and people freezing to death on the streets. She wanted to do something to help. 

“I felt compelled to take some sort of action and proposed to my two colleagues Ashley DeMarte and Dave Wall that we undertake a cross-regional winter trek to raise awareness about the risks of winter exposure for homeless citizens and to demonstrate the scale of our region when travelling by foot,” she says. 

It was supposed to be a one-off event. The trio raised $5,000 and they were equipped with GPS devices so people could follow their journey across the region online. But funny things happen when you follow your heart, it inspires others, as well. 

“It was supposed to be a spontaneous one-time journey. Afterwards, people reached out asking if we would do it again the following year, saying that they wanted to do it too,” says Jennison. “So, I founded Waterloo Region Crossing Inc as a not-for-profit organization and began the process of scaling The Crossing Trek for public participation.”

That first step in Jennison’s journey blossomed into a popular annual event and a second summer event has since been added. 

The premier event, The Crossing Trek, scheduled for Feb. 8 and 9, takes participants on a 65km non-stop journey across Waterloo Region to raise awareness about the risks of exposure for homeless citizens. 

“There's such simplicity in walking, but when you've taken enough steps over a long enough amount of time, the simple act of walking acquires intention,” Jennison explains. “Walking long distances for a specific purpose has the power to inspire and challenge in a way that fosters perspective and growth.”

Jennison started adventure racing in 2010 and she’s competed in single-day races as well as expeditions up to six days long. She called on her friends in the adventure racing community to help pull the event together, and she is particularly thankful for the help of Mike Varieur and Rob Horton from the Muskoka River X ultra paddling event series as well as backcountry rescue expert Brad Baumber who has been the head of trek safety and logistics since the beginning. 

The first event had more than 100 participants and crew embarking on the journey, and we collectively fundraised over $45,000, which was invested in the construction of a new transitional housing and medical facility for homeless citizens. And it is growing still. 

“It’s developed quite organically into a community-wide event that involves hundreds of people ranging from trekkers and volunteers to donors, companies, event sponsors and landowners,” says Jennison. “The purpose of the event has always been a call to action for citizens to better understand the complexities of our community, so we can empower and uplift each other.”

In addition to The Crossing Trek, Waterloo Region Crossing has also developed an education curriculum called "Checkpoints!" to engage youth in community goodness, there is a documentary film about the project that's currently in post-production and a summer adventure race event in support of the Sexual Assault Support Centre.

That event, the Race Across Waterloo Region (RAWR), was piloted in the summer of 2019 raising about $6000, which translated into 120 counselling sessions for survivors of sexual trauma. In 2020, it will become a full-fledged race for 100 participants. 

“My hope is that participants learn something about their community and about themselves,” says Jennison. “I hope they experience humility, compassion, empowerment, and a sense of accomplishment. I hope they meet new people on the journey and help each other through their challenging moments.”

The course for the Crossing Trek follows the Grand River trail systems on a combination of two trails: The Walter Bean Trail and The Grand Valley Trail. There are now three distance options in an effort to make the event as accessible as possible. The Pioneer trek is 10kms and ends near Pioneer Memorial Tower, a national historic site in Kitchener. The Optimist trek is 28km long and ends at the Stanley Park Optimist Area, a site that was re-naturalized by The Optimist Club to how it would have been approximately 100 years ago. The Full Trek is 65km long and ends near The West Montrose Kissing Bridge, the oldest covered bridge in Canada. 

“The trek is one of the most challenging, fun, and rewarding experiences I have ever had in my life,” says Michael McCarville, a full trek participant. “It was something I don't think any of us will ever forget.”

For 2020, Jennison is hoping to recruit 300 trekkers.  The event is non-competitive so participants are fully supported including two RVs equipped with medical crew operating as mobile aid stations. As a result of the makeup of the event, and the philosophy behind it, the vast majority of participants have never done anything like it. 

“Many had never even done a 5K run,” says Jennison. “Offering a range of distance options and a support structure certainly opens up the event to a broader range of people at a range of experience levels. We have participants of all ages and backgrounds.”

Registration for the trek closes Jan. 18. For more information go to




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