Top 10 Reasons to Be a Walk Team Captain at Winter Walk 2027 Boston

Team Brookview House at Winter Walk 2026 Boston

Looking for a meaningful way to get involved with charity walks in Boston? Winter Walk brings people together to walk, fundraise and take action to end homelessness. A Winter Walk team gives people a reason to come together outside of their usual routines and do something meaningful together. Every dollar raised at Winter Walk goes directly to our nonprofit partners working to support people experiencing homelessness and help people move into stable housing.

We have a goal of having at least 200 walk teams at this year’s Winter Walk Event, and we’re looking to our walk community to help us reach that goal.  On average, structured fundraising teams raise significantly more money—often up to 10 times as much as an individual participant acting alone. With a $1 million fundraising goal for Winter Walk 2027 Boston this year, we’re going to need your help to get there! 

Here are our Top 10 Reasons to Be a Winter Walk Team Captain in 2027 

1. Because you can turn caring into action.

Most of us care about homelessness. Being a Winter Walk Team Captain gives you a simple way to move from caring to doing. You bring people together, walk with us and help raise money for organizations working every day to end homelessness and help people find a path home.

2. Because sometimes people just need someone to ask.

Your friends, family and coworkers may want to help, but they may not know where to start. You can be that person. A simple “Will you walk with me?” can turn good intentions into meaningful action.

3. Because your impact grows when you bring people with you.

You can make a difference on your own. But imagine what happens when you bring 5, 10 or 20 people with you. As a Team Captain, you're creating a community of people who are all taking action together.

4. Because you don't have to be a fundraiser to be a great captain.

You don't need a huge following or a fundraising track record. Your first job is simply to invite people to join you. We'll give you the tools, ideas and support to help your team fundraise from there.

5. Because there's power in walking with community.

There's something different about showing up shoulder-to-shoulder with people you care about for a cause that matters. You talk. You laugh. You walk. You meet new people. And for a few hours, a group of individuals becomes something bigger.

Team FamilyAid at Winter Walk 2026 Boston

6. Because your team can support the people doing the work every day.

Winter Walk isn't about solving homelessness in one day. It's about making sure local nonprofits have the resources they need to help people experiencing homelessness in Boston and help people move into stable housing. When you build a team, you're helping direct more resources toward that work.

7. Because you can bring your whole community with you.

Your team can be whoever matters to you: family, coworkers, neighbors, friends, a running club, book club, school or faith community—or simply people who believe everyone deserves a place to call home. There is no one“right” kind of Winter Walk team.

8. Because you can start small.

You don't need 50 people. You don't even need 10. Start with yourself and invite one person. Then invite another. Every team starts with someone willing to take the first step.

9. Because you can make it a tradition.

Maybe this is the year you start something: a group of coworkers who walk together every winter, a family tradition, a group of friends who reunite each year or a neighborhood team that grows over time. Being a captain gives you the chance to create something that lasts beyond one event.

10. Because your first step might inspire someone else's.

Leadership doesn't always look like a title. Sometimes it looks like sending the first text, creating the team and saying, “I'm doing this. Who's coming with me?” Your willingness to lead may inspire someone else to get involved, become a fundraiser or start a team of their own.

Last year’s top fundraising team, Temple Beth Elohim, was captained by Bud Schram. We featured him in our 2026 impact report. Here’s what he had to say about why he walks with us: 

“I captain the Winter Walk Team because I believe that housing is a human right. As a VISTA volunteer in Washington DC in 1968, I was shaken to see makeshift shacks set up on the Washington Mall. Little did I believe that we would still be combatting homelessness, poverty and racial divide six decades later. This shocking fact was my motivation to lead the Temple Beth Elohim Racial Justice Initiative's Winter Walk Team.

As someone who does not experience homelessness I am committed to bringing an end to homelessness by raising awareness and providing financial support to help eradicate homelessness in the Greater Boston Area. I am grateful to support such a vital mission by bringing together a Multi Generational Team of walkers from Temple Beth Elohim. Our TBE Team embodies the essence of Tikkun Olam (Repairing the World) by addressing one of the most urgent challenges facing our neighbors, listen to their stories, show that we care about their lives and do what we can do to ease their struggles.”

As a Team Captain, you have the power to bring people together, turn good intentions into action, and help your team raise as much money as possible for local organizations working to end homelessness. Every great Winter Walk team starts with someone willing to say, “I’ll lead the way.” Is that you?

You don't have to be a great fundraiser. You just have to be willing to bring people together.

Be the person who sends the text. Starts the group chat. Asks your coworkers. Invites your family. Gets your friends together.

Be the person who says, “Let's walk.”

We'll help you take it from there.