Sometimes an issue seems too big to be able to fix. Often we feel powerless because of the number of factors involved. Even with that feeling, we can find ways to make a difference.

An article about homelessness in our community brought Tessa Jennison to action. Jennison had read the story while working at a startup in the Accelerator Centre. “The homelessness problem has gotten worse. The Region's affordable housing list has a nine-year waitlist. Winter is life-threatening,” said Jennison.

Lack of affordable housing is one of the issues. Mental health and addiction are also factors.

Jennison told her two colleagues she wanted to do something. “But what?” they asked.

Homelessness is a huge, complex issue. So Jennison suggested they go for a walk.

That walk sparked the creation of Crossing Trek, a walk across Waterloo Region to raise awareness of the risks of exposure for homeless people, and to raise money for local organizations trying to fix homelessness.In its first year,Jennison and her two colleagues trekked to raise $5,000. When  supporters asked if there was going to be another trek, Jennison formed a non-profit to expand the event. In 2018, it grew to include more than 100 participants and crew. They raised $45,000 from more than 8,000 donors with the funds going to the Working Centre in Kitchener. The money supported transitional housing and medical services at 115 Water St..

“It's an issue that’s not sexy,” Jennison said. “People are uncomfortable thinking about it. People feel shame and guilt. Privilege guilt. Someone is sleeping in a snowbank when you're going home to sleep in a warm house.” 

The issues can feel huge and daunting. But Jennison believes that as a community, we can produce tangible results. “Go on the trek or sponsor someone who is. Be a corporate sponsor,” she said.  

Jennison is expanding the Crossing Trek in 2020 to include 300 people with a fundraising goal of $100,000. The funds will support a long-term affordable housing project, which is in early stages of development.

“This walk started as a way to shift perspectives. From an urban planning perspective, I see a potential to reprioritize these issues,” said Jennison, a graduate of the University of Waterloo’s School of Urban and Regional Planning.

The trek shows how long it takes to walk through the region in winter, an activity Jennison believes we lack perspective on.

“The simplicity of it was easy to absorb. People could follow online and see how long it took to make the journey on foot. It offers a sense of perspective on what distance is like for a different mode of travel.”

Jennison noted that while the trek is a way to shift perspective, participants don’t experience what it is like to be homeless and travel on foot. “We have a mandatory gear list and safety teams with us – and we have homes to go to at the end of the trek.”

Gentrification continues to push at-risk people farther and farther out from the core, making it increasingly difficult for them to reach social services. “It takes longer to get to services,” Jennison said. “The journey can be challenging in the winter time.”

She cited Seattle as an example of a knowledge city, similar to Waterloo Region, that didn't do enough to prevent homelessness early on. “Today, they continue to have a huge problem with homelessness,” said Jennison, who wants to see us focus empathy and compassion to address the problems here.

She also looks at affordable housing and addiction treatment as priorities. “We can focus on social compassion at the same time we build our reputation as a tech community,” Jennison said. “These issues can spiral out of control. There is no going back at that point.”

Visit to learn more about how you can get involved as a participant or a sponsor.

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While you’re strapping on your hiking boots, I see and hear that...The Kitchener-Waterloo Art Gallery has Feast for the Senses 10 on Thursday, Nov. 14 from 7 to 10 p.m. It's an evening of tapas and drinks, with a tour of the works of Adad Hannah before a meal and tasting menu from Chef Dan McCowan and Sommelier Ainsley Szvitak of Red House. The Lions Club Santa Claus Parade is on Saturday, Nov. 16 starting at 10:30 a.m. The Apollo Cinema has Interactive! Willy Wonka on Saturday, Nov. 16 starting at 4 p.m. There's bags of special props and other surprises.