The Winter Walk Founding Story

You can watch a video here about my founding of the Winter Walk.

My earliest memories of homelessness in Boston were downtown near the train stations when I was in high school. I remember being disturbed by the scene, but did not know what I could do.

Many years later, I was driving by Albany Street with my four year old son Michael, and when we came to a red traffic light, there was a homeless person sleeping on the side of the street. Michael became agitated, and asked me to check on the man. I did, and also made a mental note to start paying more attention myself.

Around 2003, my mentor Thomas J. White asked me to visit Sojourner House for homeless families in Boston. This visit turned into what is now a long-time interest in the problems of homelessness. Over the years, I became a donor to homeless service organizations, and volunteered at Pine Street Inn and also at Greater Boston Food Bank. My friend Kel Kelly has also been a strong advocate for the homeless, and it was always inspirational to watch how she interacted with people who live on the street.

It was not until a meeting with Dr. Jim O'Connell in 2014 that got me thinking about doing something to raise greater awareness of homelessness in Boston, with the goal of raising more funds to support more programs.

In 2016, I created the Winter Walk for Homelessness with Ari Barbanell and Robyn Glaser.

The idea was to have one morning a year where we hoped to get thousands of participants to hear first-hand stories of homelessness, to then do a two mile contemplative walk from Copley Square to and around the Boston Common and back, and finally to be introduced to homeless service organizations where people could donate or volunteer.

2024 was our eighth year, and we had 4,000 walkers, and several service organizations including Boston Health Care for the Homeless Program, Boston Medical Center, Bridge Over Troubled Waters, Brookview House, Pine Street Inn, and Y2Y Harvard Square. We have raised millions of dollars to support homeless service groups in Boston.

For more information, see The Winter Walk.

See other founder stories.