Hike for the homeless on the ‘coldest night of the year’

Formerly homeless herself, Carolyne Masinde will be joining the Forest Hill contingent for The Coldest Night of the Year walk on Feb. 25, a Canada-wide fundraising event on behalf of those without homes.

Masinde, a refugee from Uganda, landed in a shelter soon after arriving in Canada, where she didn’t know anyone.

Though she was grateful to be safe, her new accommodations felt like a prison, she says. There were set times for every process in the shelter: when the lights turned on in the morning, meal times, curfew, bedtimes. The incessant conflicts  — from yelling to fist fights, sometimes  incurring police visits — were also suffocating.

“It’s a hopeless situation,” she says. “You don’t have control of anything.”

Sadly, Masinde is not alone.  According to the Homeless Hub, there were more than 18,000 homeless people in Toronto in 2021.

Ve’ahavta, a Jewish non-profit based in North York, is hoping to change these grim statistics.

The organization provides a regular outreach van supplying the homeless with basic necessities like hot meals and warm clothes. It also shores up their clients’ confidence through life skills training as well as work internships.

An important source of Ve’ahavta’s revenue is The Coldest Night of the Year fundraiser.

Executive director Cari Kozierok anticipates the walk, which starts at 1700 Bathurst St., Beth Tzedec Congregation, will raise money, draw attention to homelessness, and show politicians that Torontonians care about the city’s mostly invisible inhabitants.

She hopes that walking a mile in the shoes of the homeless will deepen participants’ empathy for their plight.

“When people are freezing their tush off, it makes them think, ‘Wow, I’m going to go home and I’m going to warm up,'” Kozierok says. “But other people aren’t as fortunate.”

Donna Assh, captain of the Mosaic Outdoor Club walkers, is already plugged into this issue. The retired psychologist is impelled by the concept of tzedakah, or charitable giving, a core value of Judaism.

“I’m very philanthropic,” she says. “And I try very hard to impart that to other people.”

The spectre of homelessness has hit relatively close to home for Assh.  She knows several people who suffer from mental health issues, but are fortunate enough to have family to advocate for them and enough money for medications.

“If they didn’t have that safety net, they would also be out on the streets,” says Assh.

Witnessing the struggles of homeless people can be tough, she says.  But there are many ways to help, from volunteering on an outreach van to walking five kilometres in the cold.

Any individual contribution is small, Assh says. “But it’s a contribution.”

Grateful every day

These contributions to Ve’ahavta have turned around Masinde’s life. After she was accepted into its Life Stabilization Program, the agency found her counselling to relieve her anxiety, helped her establish immediate and longterm goals, and procured housing, she says.

Most importantly, Ve’ahavta made her believe in herself once again.  Before her stint at the non-profit, the introverted Masinde never raised her hand to speak at school. But after learning the tricks of public speaking, she began presenting with ease.  This skillset came in handy when she started interviewing for jobs, and scored multiple offers.

“Ve’ahavta created a path for me to access the person that I am,” Masinde says, “I am grateful every day.”

Today Masinde is thriving. She is working both as a case manager at LOFT Community Services and as a shelter support worker with YWCA, and she has applied for her Masters in Counselling and Psychology at the University of Toronto.

“The sky is the limit for me,” she says.

Masinde is touched by all the participants in the Coldest Night of the Year walk who are helping galvanize these changes for others.  There are 13 locations in Toronto hosting the walk, and over 2,000 participants are expected to hike either two of five kilometres on behalf of the city’s homeless.

“It’s such a show of humanity,” says Masinde. “It’s the right thing to do.”

For a list of locations of the Coldest Night in the Year Walk, as well as how you can support the walkers or register for the event, see