The Winter Walk

18/05/2026

A web of interrelated social failures in the city of Chicago has left more of the most vulnerable community members sheltering on the train.

So every Wednesday night, outreach workers from our Chicago Organizational Partner The Night Ministry gather at the CTA Red Line’s terminal on the city’s North Side to meet this vulnerable community where they are at. On Thursday nights, they do the same at the Blue Line’s terminal stop in the west Chicago suburb Forest Park.

They typically engage with roughly 200 people, according to David Wywialowski, the director of outreach and health, but the numbers fluctuate based on the weather.

Learn more about this outreach program here: https://progressive.org/magazine/on-chicagos-trains-homeless-outreach-workers-meet-people-where-they-are-mcdonald-20260420/

14/05/2026

Boston Health Care for the Homeless Program's street encounters aren't an act of charity, but a clinical necessity.

We are honored to partner with them to support the invaluable work they do in our community.

https://www.bhchp.org/news/in-boston-street-psychiatrists-are-meeting-patients-where-they-sleep/

04/05/2026

Thanks to Fox 32 Chicago for joining us at this year's Winter Walk in Chicago! Hear from our keynote speaker Reggie, our execuitve director Paulina, and Doug from organizational partner The Chicago Help Initiative in this story.

5 likes, 2 comments. "Winter Walk Chicago 2026"

27/04/2026

Curious about what the U.S. Department of Housing and Urban Development recent policy shifts means for our country's homeless community?

This Shelterforce article by Dr. Garrett L. Grainger, a research fellow of social inclusion at Wrexham University in Wales, interviews dozens of boots-on-the-ground administrators to give you a firsthand look into how dire these changes and budget cuts really are.

https://shelterforce.org/2026/04/20/what-huds-new-homeless-policy-looks-like-on-the-ground/

24/04/2026

After Pete's mom passed away when he was just six years old, he found himself in and out of foster care between Sacramento, California and Cape Cod before eventually ending up living on the streets.

Read Pete's story, which he generously shared with us on our blog:
https://winterwalk.org/blog/2026/4/21/positive-petes-story

We are so thankful for the work that organizations like Commonwealth Land Trust and Hope House Boston do for the homeless community in Boston. With their support, Pete is housed, has secured his GED, and is now mentoring others who have experienced similar hardships.

23/04/2026

Did anyone else see or hear about the runner in a full suit and tie completing the Boston Marathon? He was doing it for the (right kind of) attention. Read Maurice's story here: https://www.wcvb.com/article/man-runs-boston-marathon-in-suit-and-tie/71077101

21/04/2026

If we’re serious about solving homelessness, we need solutions that match the complexity of the problem, but how's this for a powerful example of what lived experience brings to the table in the fight to end homelessness.

This New York City restaurateur who, after experiencing homelessness himself, is now offering shelter and support to others through his restaurant. What began as a personal act of compassion - providing meals and a place to rest - has grown into a lifeline for people with nowhere else to go.

On cold nights, the restaurant’s heated entryway remains open to those in need.

13/04/2026

Our Boston Organizational Partner Circle of Hope has an ever-changing list of priority clothing and hygiene essentials for the community they serve. Here is the latest and here is how to donate: https://www.circleofhopeonline.org/howtohelp/

13/04/2026

There is still time to join us for Hearth's 2026 Annual Meeting. Hear from our honored guest speaker Joyce Tavon, CEO of the Massachusetts Housing and Shelter Alliance, reflect on a year of our mission in action, and help us celebrate this year's Hearth Housing Champion Award recipients. Register and learn more at hearth-home.org/2026-annual-meeting

10/04/2026

Homelessness is not a measure of someone’s worth or potential and the proof is in the greatness of this list. https://www.forbes.com/sites/jessicajacolbe/2026/04/09/once-homeless-they-are-now-among-the-nations-most-successful-self-made-americans/

How these entrepreneurs and entertainers went from sleeping in cars and flopping on friends’ couches to becoming some of the most successful people in America.