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School on Wheels of Massachusetts

Ending the cycle of homelessness through education.

School can be challenging enough for students today, but when they are homeless, it adds an entirely different level of difficulty. And that’s where School on Wheels of Massachusetts comes in. Stop & Shop has supported this nonprofit through the Community Bag Program.

Tell us about School on Wheels of Massachusetts.

Here at School on Wheels, we support the academic, social and emotional growth of students impacted by homelessness. We serve students in the Commonwealth of Massachusetts.

We have positive, caring adults to tutor students affected and impacted by homelessness in an after-school setting.

We were founded in 2004 by teacher and child advocate Cheryl Opper. She was a schoolteacher in the Easton, Massachusetts, Public Schools System. She realized that no matter what community you are in, students and families are impacted by homelessness. It started in her basement collecting backpacks. The program quickly progressed to tutoring students in multiple shelters, primarily in the Brockton, Massachusetts, area, and then grew to Southeast Massachusetts. Fast forward to today, we’re in over 20 locations tutoring students. The idea of School on Wheels is for our team to bring the tutoring service to you. We have positive, caring adults to tutor students affected and impacted by homelessness in an after-school setting.

What services do you provide to the community?

It starts with a backpack. Towards the end of the summer, most families go back-to-school shopping, and they’ve got lists from their teachers of what supplies they need. Often, a backpack with all the supplies needed for one school year can be hundreds of dollars. Unfortunately, sometimes it’s deciding between dinner or a fully stocked backpack for school. We want to take that burden from our families.

School on Wheels partners with the local school systems for our backpack program. They help us identify the students in need, and we’re putting together thousands of backpacks throughout the summer. Then the schools help deliver them before the school year starts. We never want to hear that a student doesn’t have a backpack or a notebook. Kids should always feel prepared on the first day of school. To be able to give students the confidence that they are ready for school is such a blessing. We’re proud to have given out over 7,000 backpacks in Massachusetts this fall.

From there, our tutoring program comes into play. Our volunteers tutor students during the school year, kindergarten through high school; then, we transition students to our Bridge Mentoring program, where we partner college-age students with an adult mentor. These volunteer mentors come from various types of professional industries and age demographics. They guide what life will be like after high school, helping students set career goals and navigate the tricky path of education and how it could help advance their career goals. In addition to the mentor, we also provide students with financial assistance to eliminate any roadblocks to their education. We’re fortunate to have about a hundred students a year in our Bridge program and help them overcome those barriers to their education.

We want to be there for our students and frequently go beyond what you think is traditional financial assistance for education. We offer help so that little obstacles don’t add up and deter our students from their long-term goals of staying on track and getting their education. For some of our students, we help with tuition for driver’s ed because they have part-time jobs and need transportation.

What sets you apart from other nonprofits in your community?

School on Wheels lives by the pillars of child education and the empowerment of families affected by homelessness. The organization is primarily about student education, but it doesn’t stop there.

If a student’s family needs support, we are there. Let’s say, for example, that a family is moving from one shelter to another or from one shelter to an apartment; we will help them. We’re there for our families when they need us. Our volunteers and staff go above and beyond to empower the families of our students for success. And that family empowerment sets us apart.

Tell us a story that illustrates the good work of your organization.

It is challenging for refugee families coming to Massachusetts. Our community partners have raised their hands and said, yes, we’ll provide shelters for these families. Often these families are housed in shelters and because of overcrowding, more recently they are housed at hotels. We are asked to help the students in these families as they encounter language barriers and enter into a new public school system.

We are currently serving at a hotel in Kingston, with an open house night. Forty-four students signed up. It was amazing. When we do School on Wheels open houses, we provide pizza, which is usually why people go, and then they sign up for tutoring. At this most recent open house, our team was setting up the pizza station and a station with books and toys. And all the students passed over the pizza and went straight for the books and toys. We were pleasantly surprised.

We started tutoring the first night during the open house. They were just so eager to learn and get some help. I worked with a group of kindergartners by reading to them. Someone who is reading along with them and helping them understand the words is a great way to learn English. During this session, I was reading a story about an eagle. Every time one little girl saw the eagle, she would put her arms out like she was flying and say, “Eagle fly, eagle fly!” It was the cutest thing. These events are where it starts for our students.

Our annual gala also presents success stories that we are proud to share. One of our Bridge Program students is asked to speak and tell his or her School on Wheels story. Last year we had a young man named Candido share how he found School on Wheels. We partnered him up with a mentor. He ended up enrolled in UMass Dartmouth in an engineering program. Our team helped him with financial assistance, books for school and gas cards because he worked a part-time job while in school—anything to help him stay on track to achieve his goals.

Candido was getting ready to graduate, so his mentor was helping him with interview prep. And I remember giving him my suit jacket because I noticed we were the same size. He called a couple of weeks later to say he got a job offer. School on Wheels is proud to have helped Candido earn his degree and get a great job.

I’m fortunate to be able to do this work. It takes a community of people who want to help, whether volunteers or funders, to keep our mission going.

What is your most outstanding achievement or contribution to the community?

Every year we have at least ten high school and college graduates. Statistics show that if not for intervention from organizations like School on Wheels, students impacted by homelessness or poverty during their lives aren’t likely to graduate. We’re changing those statistics and giving these students opportunities.

Those little barriers, like lack of confidence or not knowing that they can do it, are what School on Wheels is proud to help students overcome. They just need that little support.

Positive encouragement makes a difference. A young man named Darren came to School on Wheels in the fourth grade. He worked with one of our first volunteer tutors. This tutor started working with Darren on his math; Darren would say, “I’m dumb in math. I just don’t get it.” But his tutor kept working to give him that confidence. A positive, caring role model, week after week, can get a student over that hump. Darren’s tutor stayed with him through elementary school and then began mentoring him in high school. Darren wanted to become an electrician, so we got him into a trade school. He is now in his mid-twenties, and last spring, he graduated with his electrical certificate. Darren has a great career that he loves. Darren and his mentor often would have their meetings during coffee or breakfast. Recently they went out to breakfast, and Darren was able to say, “I got this.” when the check came. They were both so proud of Darren’s accomplishments that led up to him now being able to pick up the tab.

Those little barriers, like lack of confidence or not knowing that they can do it, are what School on Wheels is proud to help students overcome. They just need that little support.

What do you want people to know about your organization?

We believe that education is the long-term solution to end homelessness. School on Wheels is here for students, letting them know they can do it. We’re providing a path to success. The way to end the cycle of homelessness is through schooling so students never need shelter or assistance from a food pantry. We aim to help students get that job and feel self-sufficient and successful.

How are you using the funds raised from the Stop & Shop Community Bag Program?

Every year we’re committed to our programs. The backpacks give students the confidence that they’re prepared for the school year, and it takes that burden off families, so they don’t have to choose between a meal or school supplies. We want to be able to say yes to a student that needs our Bridge program in college when their syllabus calls for $500 worth of books. We know statistics show that, unfortunately, most folks drop out after the first year. We want students to have positive, caring adult mentors checking in on them, letting them know to stick with it because they can do this. The Stop & Shop Community Bag Program funds will be critical to help us continue our programs

Is there anything you’d like to add?

There are many ways to get involved at School on Wheels, whether you want to help put together backpacks, stage a backpack drive in your community or become a volunteer tutor or mentor. Please visit our website for more information, We truly appreciate the donations that we receive; they help School on Wheels continue our mission!

Steve Telesmanick is Chief Executive Officer of School on Wheels Massachusetts.

Published February 23, 2023.