How to Help People Experiencing Homelessness This Winter and Holiday Season in Boston ❄️

Winter in Boston can feel magical—twinkling lights, snow on brownstones, and cozy nights in. At the same time, it can be an especially hard season for people sleeping outside, staying in shelters, or bouncing between temporary places.

If you’ve ever passed someone trying to stay warm on a cold night and wondered what might actually help, you’re not alone. You don’t have to fix everything to make a difference; even a small action can mean a lot to someone getting through winter day by day.

This guide is meant as a starting point: a few concrete ways to support neighbors experiencing homelessness in Boston during the colder months and holiday season.

1. Begin With Simple Humanity

Before we talk about donations and drives, it can help to remember that people experiencing homelessness are, first and foremost, people—neighbors who happen to be going through something really hard.

You don’t have to say or do anything elaborate. Sometimes the smallest gestures matter most:

• A quick “hey” or “good morning” instead of looking away

• A moment of eye contact and a smile

• Asking, if you feel comfortable:

  “Would you like a coffee or something warm?”

• Respecting the answer—whether it’s yes, no, or no response at all

  
  

None of this fixes the bigger systems at play, but it does send a quiet message: you’re still seen.

2. Donate to Local Organizations Doing the Work Every Day

Donations—especially financial ones—help local organizations stay flexible and respond to what people need most in the moment, whether that’s shelter, food, clothing, legal support, or long-term housing help.

Here are a few Boston-area organizations focused on homelessness and housing insecurity:

• Rosie’s Place – The first women-only shelter in the United States, Rosie’s Place is a community center for poor and unhoused women in Boston. They offer emergency shelter, meals, a food pantry, education, legal assistance, wellness care, housing search support, and more. They accept no government funding and rely on individual and private support.

• St. Francis House – New England’s largest day shelter, providing meals, clothing, counseling, job and housing support, and other services for people experiencing homelessness in downtown Boston.

• Friends of Boston’s Homeless – Partners with Boston’s city shelters to help people transition from homelessness into housing by funding move-in costs, furnishings, and stabilization support.

• Boston Health Care for the Homeless Program (BHCHP) – Delivers integrated medical and behavioral health care in shelters, on the streets, and in clinics throughout Boston.

• Horizons for Homeless Children – Focuses on early education and family support for children and parents experiencing homelessness across Greater Boston.

• Christmas in the City – A volunteer-run organization creating holiday experiences and year-round support for families struggling with homelessness and deep poverty.

  
  

If you’re not sure where to begin, volunteer hubs like Boston Cares and local roundups of donation opportunities can help you discover even more shelters and nonprofits working on the front lines.

3. Give What’s Actually Needed: Coats, Layers, and Essentials

In the winter, warmth is survival.

Before dropping bags into a random donation bin, check donation guidelines for local shelters or city programs so you’re giving items that are actually useful and welcome.

Commonly requested winter items include:

• New or gently used winter coats, especially in adult sizes

• Hats, gloves, scarves, thermal socks

• Warm base layers (long underwear, leggings, sweatshirts)

• Waterproof boots in good condition

• Travel-sized toiletries (soap, shampoo, deodorant, lotion, lip balm)

• Hand warmers and reusable water bottles

  
  

You can:

• Organize a coat or winter essentials drive through your workplace, building, or kid’s school.

• Build a few care kits (socks + snack + hand warmers + sanitizer + a kind note) to keep in your bag or car.

• Donate new coats and gifts to winter-focused programs that specialize in distributing seasonal support.

  
  

4. Volunteer Your Time (Even a Few Hours Helps)

The winter and holiday season is when shelters, day programs, and outreach teams are stretched thin—and volunteers become a critical support.

Some ways to plug in:

• Serve meals, help with clothing rooms, or support day programs at local shelters.

• Volunteer at organizations that run winter drives, holiday events, or warming centers.

• Connect with Boston Cares or similar hubs that list opportunities across multiple organizations.

  
  

If you’re new to volunteering, start small: one evening, one weekend, one event. You don’t have to do everything to do something meaningful.

5. Support Families and Young People Experiencing Homelessness

Homelessness isn’t just an adult issue—many families with children are in shelters, cars, or unstable stays with relatives and friends.

You can:

• Support organizations that create early learning spaces and “playspaces” in shelters, giving kids a safe and enriching place to be.

• Look for groups that focus specifically on youth experiencing homelessness and provide job training, employment, and support toward stable housing.

• Help with winter clothing, diapers, backpacks, and school supplies through children-focused nonprofits.

  
  

These are powerful ways to interrupt the cycle of instability before it becomes lifelong.

6. Use Your Voice: Share Resources and Normalize Helping

Not everyone can donate money this year. Not everyone has extra time. That’s okay—sharing information is also a form of support.

Practical ways to use your voice:

• Share a local organization’s donation link or wishlist on social media.

• Add a section in your workplace newsletter or Slack about a winter drive.

• If you’re a homeowner, landlord, or investor, consider:

  • Matching donations from your tenants or clients.

  • Partnering with a local shelter for a holiday drive.

  • Donating a portion of December income to a housing-focused nonprofit.

    
    

You can help normalize the idea that caring about housing and homelessness is part of being a good neighbor.

7. When You See Someone Outside in the Cold

This is one of the hardest parts emotionally—seeing someone sleeping outside on a freezing night and not knowing what’s helpful.

A few guidelines:

• Trust your instincts and stay safe.

• If you’re comfortable, you can offer something small:

  • A hot drink

  • A snack

  • A gift card to a nearby café

  • A pair of gloves or hand warmers

• If someone seems in distress or unsafe, you can look up local non-emergency numbers, outreach teams, or city services that may be able to respond.

  
  

You won’t be able to fix everything in that moment—but you can choose not to look away.

8. One Next Step

If this feels like a lot, don’t overthink it. Start with one thing:

• Pick one organization to donate to.

• Sign up for one volunteer shift.

• Buy one extra hat, pair of gloves, or coat the next time you’re out shopping.

• Share one resource with a friend or coworker.

Small actions, multiplied across a city, do add up.

From all of us trying to make home more stable, more warm, and more humane for everyone: thank you for caring, and for doing even one thing this winter.