Boston's Winter Walk to End Homelessness Celebrates 10 Years

Annual fundraiser brings thousands together to support local organizations and raise awareness

Apr. 8, 2026 at 2:03am

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An abstract, impressionistic scene of people walking together in a public park, with soft, blurred shapes and vibrant splashes of color conveying the communal energy of the Winter Walk event.The annual Winter Walk in Boston Common brings the community together to support local organizations working to end homelessness.Boston Today

More than 3,000 people gathered in Boston Common on March 22 for the city's 10th annual Winter Walk to End Homelessness. The event, co-founded in 2016 by tech entrepreneur Paul English, has grown into one of Boston's largest community events, raising hundreds of thousands of dollars each year for local nonprofits working to address homelessness. Participants donned matching blue beanies and walked a mile loop around the park before gathering for coffee, pastries, and celebration.

Why it matters

The Winter Walk is an important annual event that brings the Boston community together to support organizations providing critical services for the city's estimated 5,500 homeless individuals, particularly during the harsh winter months when cold-related deaths are a serious concern. The walk also raises awareness and funds to help address the complex issue of homelessness in Boston.

The details

The Winter Walk features a one-mile loop around Boston Common, with participants wearing matching blue beanies that have become a signature of the event. After the walk, attendees gather to enjoy coffee, pastries, and celebrate the community. The event raises money for local nonprofits including the Pine Street Inn, Boston Health Care for the Homeless, St. Francis House, and more than 20 other service providers.

  • The Winter Walk is typically held in February to coincide with Boston's coldest months, but was rescheduled to March this year due to back-to-back blizzards.
  • The 10th annual Winter Walk took place on March 22, 2026.

The players

Paul English

The tech entrepreneur who co-founded the Winter Walk in 2016 with Ari Barbanell and Robyn Glaser.

Deborah Collins

The chief executive officer of Brookview House, a Boston nonprofit that serves homeless and at-risk families, who works with the Winter Walk organizers throughout the year.

Brandy Barents

A Boston University senior lecturer who enrolled students from her service-learning course in the Winter Walk.

Darren Donovan

A first-year Mechanical Engineering major at Boston University who participated in the Winter Walk through Barents' course.

Marler Verona

A first-year Biology major at Boston University who participated in the Winter Walk through Barents' course.

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What they’re saying

“These are all the programs that spend day in and day out taking care of people and joining in a community. And then on this day, we get to all just walk together with everybody we know and love and care about. It never happens like this.”

— Paul English, Co-founder, Winter Walk

“I thought it would be a cool research class for people to not only become aware, but think about the possibilities for how we can really help in our culture and society. Winter Walk was an essential way I thought about this class happening.”

— Brandy Barents, Senior Lecturer, Boston University

“[Homelessness is] a problem that I feel like isn't talked about enough, so I wanted to learn and give perspective on what's going on in my city and learn how it's affecting people.”

— Darren Donovan, First-year Mechanical Engineering major, Boston University

“I think it gives me a bigger view on the city, and it makes me understand more of what my home is now and what my home is here. Not only has it been experienced for me to learn more about the city, but just to feel more comfortable in the home that I'm living in as well.”

— Marler Verona, First-year Biology major, Boston University

What’s next

The Winter Walk organization is looking to expand the event to additional cities beyond Boston in 2027, with the goal of building a national movement to raise awareness and support for ending homelessness.

The takeaway

The Winter Walk has become a powerful symbol of Boston's commitment to supporting its homeless population and the dedicated organizations working to provide critical services. As the event enters its second decade, it continues to bring the community together around this important cause, inspiring others to take action in their own cities.