A sea of blue beanies marched through the streets of Boston Common on Sunday morning to support the 8th annual Winter Walk and raise awareness for people experiencing homelessness. Event organizers in neon-green beanies cheerfully supported the crowd as the participants went on their two-mile walk around the perimeter of the common.

The Winter Walk is a non-profit organization based in Boston, founded by entrepreneur and activist Paul English in 2016. The Winter Walk harbors the belief that ending homelessness is a goal within the organization’s reach. The Winter Walk’s mission is to raise money and advocacy to eradicate homelessness.

This year’s walk in Boston had roughly 4,000 people who signed up to participate in the event. From 2023 onwards, the Winter Walk has expanded to having walks in Western Mass and New York City.  

Mike Falco, a resident of Swampscott, was participating in the Winter Walk through Saint Cecilia Parish, which sponsors members to participate in the annual walk. 

“In a country that has so much excess wealth, you also have people that don’t have anything, that don’t even have a place to get inside in the cold,” Falco said. “[The walk] sends a good message. At least, hopefully, people know that people do care about them.” 

The kickoff ceremony was hosted by a series of supervisors, multiple guest speakers, and event organizers speaking to walkers about the Winter Walk’s message. Dr. Jim O’Connell, the president of the Boston Health Care for the Homeless Program, addressed the crowd with a warm welcome, sharing his experience with helping the city’s homeless population and how the Winter Walk started through a conversation he had with Paul English. 

“It was really cold, and we saw these people sleeping on benches right along Fort Point Shelter,” O’Connell said. “I remember Paul was looking across at one of his offices and saying, ‘You know, how can we allow this [to happen] in a city like this or any city around the country?’”

O’Connell recounted that English’s idea for a Winter Walk would allow participants to walk in the cold with people who have experienced homelessness to understand what it is like to be outside in such harsh temperatures. 

O’Connell continued his speech by highlighting the almost-two dozen partner organizations that support the Winter Walk before introducing Boston Mayor Michelle Wu to speak. 

Wu said she was very grateful for the work of advocates and supporters and mentioned how Boston’s work to eradicate homelessness stands out among other cities across the country. 

“The work that we’ve done to build low threshold supportive housing is to make sure that we are continuing to add to the number of spaces and places where people can find warmth, shelter, support and most importantly, community,” Wu said. 

“Everyone in Boston is standing together as one to say we are gonna do this and end homelessness,” she continued.

Amanda Grant-Rose, the Winter Walk’s deputy director, came on stage following Wu to introduce Sarah Reed, who has faced homelessness multiple times in the past, and ask questions. Now housed, Reed has come to the Winter Walk to share her story with the community of participants. 

Reed talked about how she faced homelessness after a painful divorce, spending six months living in her van while working two jobs and not being able to earn enough income to afford housing. After getting back on her feet, she faced a breakdown that caused her to leave her job, which, once again, left her unhoused. After this experience, she went to a shelter to get help, which she said was a disempowering experience for her. 

“I felt like I was processed like a criminal when I first went in, and my picture was taken and sent right to the police department, and I’m like, hey, you know, I’m just here for help,” Reed said. 

Reed shared how becoming involved with people and organizations affiliated with the Winter Walk was part of why she could turn her life around and why she chose to speak at events that raise awareness about the homeless. 

“Hearing the stories of other people and feeling outraged about [homelessness], when I get chances to speak, I can’t necessarily feel good about speaking for myself,” Reed said. “But then I think about the people I’ve met, and I’m like, no, somebody has to speak for these people.”

 English gave a short speech about the importance of this year’s crowd, connecting with the partnered organizations to further the impact of the organization’s reach in the fight to end homelessness.

“Today is really important, but we also want to make sure that this is a catalyst for what’s going to happen for the rest of the year,” English said. “So if as many of you as possible can make a connection with any organization here, that would be fantastic.” 

Following English’s speech, the walk commenced, with the walkers moving in a massive cluster towards their route. While on the walk, organizers and staff prepared breakfast and live music by upcoming artist Samantha McKaige for the event participants.

While setting up, Event Organizer Delphia Bizzell shared the story of how they got involved with The Winter Walk. Bizzell has lived in the Boston area for six years, in their first two years they were homeless living in a shelter. Bizzell talked about her experience with the Winter Walk.

“I love it. It’s a big part of my life.” Bizzell said. it’s just a great experience and to bring all these people together and everybody walking side by side…”

Bizzell being a former homeless person themself, shared what people can do besides going to events like the Winter Walk to help homeless people. 

“[People don’t] realize that not every homeless person is a drunk or an addict because no one wakes up saying ‘Today, I want to be homeless,’” Bizzell said.

She continued, “There’s many different people out there who are homeless, and they’re not strangers.

They’re just people who have hit a rough spot in their life and are just not looking for a handout, but looking for a leg up.”