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Take it From Them

"Take it From Them" profiles community leaders, entrepreneurs, business owners, and artists who have inspired change, brought communities together, and made valuable contributions to their professions.

Interview with Cheryl Opper, Founder of School on Wheels of Massachusetts (SOWMA)

Updated: May 23, 2023

First published May 23, 2023

By Ruthann S Baler

School on Wheels of Massachusetts (SOWMA) is a private, nonprofit 501 (C) (3) organization that supports the academic, social, and emotional growth of students in grades K-12 who are impacted by homelessness. SOWMA was founded in 2004 by teacher and child advocate Cheryl Opper after she read a magazine article featuring Agnes Stevens, a retired teacher in Southern California who saw hundreds of children on the streets in Los Angeles during school hours. After learning their families were living out of cars on Skid Row, Agnes and a group of friends gathered books and school supplies and helped the parents enroll their children in school. The group provided school uniforms, filled backpacks, and tutoring, which led to the founding of School on Wheels.

Cheryl Opper, founder of SOWMA, is pictured with former student Zach as they celebrate his graduation from Bridgewater State University in Bridgewater, Mass. Zach received a scholarship from BSU, studied abroad for one year, was inducted into the National Math Honor Society, and received his Chartered Financial Analyst license while earning his MBA from the University of Houston.

Inspired by this activism, Cheryl set out to bring School on Wheels to Massachusetts. Within several months, she started SOWMA from the kitchen of her Easton, Mass. home. Family and friends helped fill backpacks with donated school supplies for 20 children living at two family shelters in neighboring towns.

Today, SOWMA distributes approximately 7,000 backpacks each school year to homeless students living in 38 Massachusetts communities. Along with donated backpacks, hundreds of trained volunteers provide one-on-one tutoring to approximately 300 students at 18 program locations from Boston to Massachusetts’ east coast. SOWMA’s Bridge Mentoring Program provides nearly 100 high school and college-age students with financial support and mentors who guide students throughout their high school careers and into their post-secondary plans, including college, vocational training, and job placements. SOWMA’s core program areas include backpacks/school supplies, tutoring/mentoring and post-secondary educational assistance. 

Since SOWMA’s founding, Cheryl has received numerous awards including the MVP Community Service Award from the New England Patriots and the Bank of America Local Heroes Award. Cheryl retired in 2018 and continues to serve on the advisory board, advocating for SOWMA and the growing need to provide educational support to children experiencing homelessness.

Cheryl, what was it like during those first few years?

Exhilarating, scary and exhausting, like a roller coaster ride. Although I was an educator, I knew very little about child homelessness in our state. Initially, I did  a lot of research and homework. I learned who the homeless shelter providers were in my area and which school administrators, educators, nonprofits, and businesses I should contact.  I reached out to the homeless liaison with the Massachusetts Department of Early and Secondary Education to find out how many homeless children were living in my backyard and surrounding communities. The first few years were all about networking and building relationships to create a village of support for SOWMA’s mission. I spoke to rotary clubs, churches, temples, schools, banks, and companies to share information about the critical need to support students impacted by homelessness. People were shocked to find out that there were over 20,000 identified students in grades K-12 experiencing homelessness in Massachusetts.

Those first few years, I would work straight through the night. When my husband was leaving for work, I would be going to bed for a few hours. I was like a hamster on a spinning wheel running faster and faster, thinking about all the children in need of our services. How could we ever support all the students who had lost their homes, their neighbors, friends, safety, and security?

Then I remembered what Agnes would say: “One child at a time. There are others who want to help these children. You will create a village of love for these amazing, resilient children who will change the world.” Agnes was right. People of all ages, all backgrounds, and all races were reaching out to help. They saw the need and responded to the call to action to break the cycle of homelessness one child at a time. My phone was ringing off the hook and I couldn’t keep up with all the email requests of people wanting to make a difference for these kids.

Cheryl reads books with several students at SOWMA’s tutoring site in Brockton, Mass.

What was your vision for School on Wheels?

I always wanted SOWMA to be a holistic, wrap-around, educational, social, and emotional support

system not just for the children, but for the parents and grandparents as well. Family members are the

child’s first teacher and most important role model. SOWMA not only provides support services for the

student, but for the whole family.  

My long-term vision was to go deeper and provide expanded services for students beyond high school. SOWMA’s board of directors agreed that if we were going to help students break the cycle of poverty, then we would need some type of higher education, vocation, or certification support services. From this vision came High School Plus, which was later called the Bridge Program. These support services help bridge the gap between high school and post-secondary education. Many of our high school students are on their own without any kind of adult support. The national statistic states one out of four homeless students will not finish high school. This sets up these students to repeat the cycle of homelessness as adults.

I am proud to say most of our SOWMA students graduate high school and move on to vocational training programs or to college. We have student alumni who are nurses, social workers, teachers, lawyers, hair stylists, electricians, and so much more. Some of our alumni return as mentors and tutors to pay it forward.

What were some other challenges?

Families experiencing homelessness move multiple times, sometimes three to five times in one year. Some families are in a shelter for a year, others are there for only a few weeks before moving to another temporary place. SOWMA needed to figure out how we could support students after they move. After lots of planning, researching, and raising funds, we set up tutoring sites at transitional housing units, local libraries, and businesses to provide a safe space for students to continue their tutoring. 

Homeless students experience huge gaps in their education because of multiple moves, school absences, mental health issues, lack of food security and sleep, different teaching styles, and loss of friends and school activities. SOWMA’s mission is to fill those educational gaps while providing the emotional and social support children need to soar above their losses and challenges. 

In 2008, when the markets crashed, the shelters were filled to capacity and hundreds of families were being housed in motels. This meant SOWMA had to start a new model of tutoring in the motels if we were going to help these students. Over the years the number of families we were serving doubled, tripled, and eventually increased 100 percent. The huge influx of immigrants in recent years has also increased the need for our support services. The need for more volunteers who speak the language of our immigrant students is urgent right now.

Tell us more about Agnes Stevens, who founded School on Wheels in 1993.

Agnes was my number one inspiration and mentor. Her whole life was about helping others, especially children. As a retired schoolteacher, she clearly understood the critical need to help students impacted by homelessness stay on track in school. She also understood the unique challenges homeless children face. She was extremely humble and kind to everyone she met. When she came to Massachusetts in 2004 to help me set up School on Wheels, she insisted on staying at a Holiday Inn where some of our homeless families were living. She wanted to talk to the parents and hear what the challenges were for their children. She taught me that volunteers are just important as the children you serve. You have to love and support them as much as you do the children. This is how you build and grow your village of love.

Cheryl is pictured with her mentor, retired teacher Agnes Steven, who founded School on Wheels of Southern California in 1993 after observing hundreds of children on the streets in Los Angeles and learning their families were living out of cars on Skid Row.

Tell us about some of your most memorable and rewarding moments over the past 20 years.

A top highlight for me was attending the high school graduation of our first SOWMA student. When we first met Darren in 2004, he was in fifth grade and failing most of his classes. Darren and his mom were living in a crowded family shelter and Darren had missed a lot of school. On the first night of tutoring, he

told his tutor Steve he was just a dumb kid that hated school. Steve, a middle school math teacher, brought a chess set to tutoring one night. With big eyes, Darren told his tutor, “I can’t play chess -- that is for smart kids.” His tutor said, “You are a smart kid, but you have missed a lot of school. I’m going to help you fill in the gaps and teach you how to play chess.” 

Darren became a strong chess player who even beat his tutor a few times. He moved out of the shelter after a few months, and we lost touch with him for two and a half years. His mother contacted us when he was in the eighth grade and said they needed our help. They had moved eight times between sixth and eighth grade. Darren was drowning in school and his self-esteem was very low. 

His tutor and I met with his new school counselor, principal, and teachers, and set up a plan for Steve to work with Darren after school at a local pizza place. Darren and his mom finally moved into an apartment in a new town and Darren repeated eighth grade at our suggestion. Steve continued to tutor him in eighth grade and all through high school. Darren became a math tutor for his peers. Steve and I proudly sat in the front row of Darren’s high school graduation. With tears in our eyes, we cheered for our first student when he crossed the stage to receive his high school diploma. Afterwards, we were invited to his family celebration where Steve presented Darren with a chess set. Darren went on to enroll in an electrician apprenticeship and joined the union. Steve and Darren continue to play chess, 19 years later.    

Another stand out memory is when I first met Zach, a student who became homeless after his mom died from cancer. Zach’s family had experienced homelessness a few times because of domestic violence, which is often the case for many of our single moms.  Zach’s high school guidance counselor introduced him to SOWMA. We helped him apply for the Bridgewater State University Scholar program. He was awarded that scholarship, which provided room and board, tuition, books, and the opportunity to study abroad in South Korea for a year. While living in South Korea, Zach taught English, studied at the university, and made many new international friends. Zach was inducted into the National Math Honor Society and joined many clubs and programs while at BSU. He went on to complete his Chartered Financial Analyst license while getting his MBA from the University of Houston. He’s now living in Houston and working for a wealth management company, has his own apartment, a car, and a cat. He spent Thanksgiving with us last year. Zach has become family over the years.

What if someone wants to start a School on Wheels or another nonprofit in their community?

My advice is to surround yourself with good people, community partners, and businesses that will support your vision and fall in love with your mission. Create a village of love and watch your dream grow.

To donate, become a mentor, or learn more about School on Wheels of Massachusetts, go to or call 508-258-9091. You can also reach Cheryl at:

1 Comment

May 25, 2023

Hello! I love your blog Ruthann! And Cheryl, your story is so inspiring! I would like to reach out to you and talk about SOWMA. Have you read "The Giver of Stars" by Jojo Moyes? It's about a team of women bringing library books via horseback during the Depression through the mountains of Kentucky. You are a decendant! Keep passing it forward, you make the world so much better! Leslie S. ❤️

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