About Us

We provide educational support to Massachusetts students facing homelessness and poverty. 

Jenevieve Dolby, Massachusetts College of Art and Design

Our Mission

Our mission is to support the academic, social and emotional growth of students impacted by homelessness and poverty.

Our Vision

The vision of School on Wheels of Massachusetts is for all students impacted by homelessness and poverty to have the academic, social and emotional support necessary to achieve a bright and productive future that will help end the cycle of homelessness.

Our Core Values

  • Educate Kids
  • Empower Families
  • End Homelessness
  • One Child at a Time

Our Impact
(Click Photo for Video)

Tutored Students
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Graduations
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Students Recieved Backpacks & School Supplies
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I stand before you as living proof that you can make it and your backpack represents more than school supplies. It's your way out.

I wholeheartedly embrace the importance of instilling curiosity and a love for learning in children at an early age. I was super excited to get to know more about SOWMA and the programs designed to help children who don't have much.

The best part of this is actually meeting the students and learning the tough hand they were dealt. They are driven, resilient, highly motivated and grateful for the support

What We Do

Our tutoring program is designed to foster the academic, social and emotional growth of students impacted by homelessness and poverty.

SOWMA’s Bridge Mentoring Program helps high school and college-age students explore educational and career opportunities.

Donations enable us to provide fully-stocked quality backpacks and new school supplies to students from kindergarten through college.

Who We Are

A community of volunteers and stakeholders who believe in the role of education in stopping the cycle of homelessness.  Collectively we strive to ensure equitable access to educational and career opportunity, empowering students to overcome barriers and achieve their full potential.  

Where We Serve

We collectively work to end the cycle of homelessness through tutoring, mentoring and backpack distribution to students living in communities throughout Massachusetts.

Tutoring Site Locations

Boston, Brockton, Fall River, Middleboro, Norwell, New Bedford, Newton, Rockland, Stoughton and Taunton.

Our History

Celebrating 22 years in 2026!

Hear the story behind our founding 20 years ago,
with Cheryl Opper and Candy O’Terry.

School on Wheels of Massachusetts (SOWMA) was founded in 2004 by teacher and child advocate Cheryl Opper after reading a magazine article about Agnes Stevens, Founder of School on Wheels of California. The article, “Lessons in Love,” described the non-profit Stevens began after noticing the many children living on Skid Row who were not attending school.

Cheryl was inspired to bring the one-on-one academic support program to Massachusetts for children impacted by homelessness and poverty. She started SOWMA out of her home in Easton, Massachusetts, where she invited volunteers to her kitchen table and filled her basement with donated backpacks and school supplies. Together the volunteers distributed school materials to 20 children living at two family shelters in Brockton, Massachusetts. Soon they began tutoring these children weekly.

During the 2025/26 academic year, SOWMA distributed more than 11,000 new, customized, grade-level backpacks to children and at-risk youth living throughout Massachusetts. Our trained volunteers tutored students living in family shelters and subsidized housing in Boston, Brockton, Fall River, Middleboro, Norwell, New Bedford, Newton, Rockland, Stoughton, and Taunton.

Our Bridge Mentoring Program provided high school and college-age students with financial support and mentors, who shepherd students through high school and onto post-secondary plans, including college, vocational training and jobs.

School on Wheels of Massachusetts is a private, non-profit 501 (c) (3) organization funded through the generosity of individuals, communities, business, corporations and foundations.

Lydia Roy, Massachusetts College of Art & Design, 2024

Diversity, Equity & Inclusion

School on Wheels of Massachusetts is committed to cultivating a diverse staff and volunteer base by promoting a culture of inclusivity and belonging.

To reflect our diverse student population, we are committed to continuing to increase diversity & inclusion throughout our organization, including staff, volunteers and Board of Directors.

  • Recruit tutors & mentors that reflect the diversity of our students
  • Provide training to support diversity & inclusion
  • Develop the Board through a diversity & inclusion lens

Recent News

07/14/2026
Congratulations to 20 Soaring 2026 Scholars Recipients   The Soaring Scholar Scholarship program just celebrated its five-year anniversary with another record-breaking year.  The Class of 2026 was awarded over $60,000 in scholarships. ...
06/25/2026
Our 2026 Volunteer Appreciation Day was inspired by the amsonia flower, symbolizing strength, resilience, and endurance. The evening’s theme was beautifully illustrated by Yiner Xu of Massachusetts College of Art and Design....

Support Our Programs

There are many ways to support our mission and make a difference in Massachusetts communities where children and youth impacted by homelessness and poverty need educational support.