In many ways, brothers Jackson, Louis, and Nicholas Cavallerano have been training for their first Boston Marathons for years as lifelong athletes and community volunteers.
For all three of these young men who grew up in Wellesley, next month’s race from Hopkinton to Boston will be their first marathon, and each is doing so through a different fundraising program.
“We are calling it Operation ‘Band of Brothers,'” says dad Chris. “Following the 2024 Boston Marathon our family was talking about how great it is to see all the charity runners and the impact one can make when you ‘run for a reason.'”
The elder Cavallerano says his sons have joined him in many community efforts over the years, such as dressing graves for veterans at Village Church and adopting fire hydrants in the neighborhood to make sure they’re clear of snow. They’ve also joined him on 5K runs and rucks for the Glen Doherty Memorial Road Race.
Chris has also set a family example for running the Boston Marathon for a cause. In 2012, he was the first Boston Marathon runner for National Braille Press and did so blindfolded (with guides).
Cavallerano family members and friends will be providing plenty of support along the course for the brothers in April.
“We hope to see them in Framingham, have a tent across from town hall/next to the library as part of Friends of Wellesley Veterans, then cheer them on in Newton along Heartbreak Hill and finally at the finish line… It’s even a race to keep up with the runners,” Chris says.
We reached out to the Cavallerano brothers to learn more about them, their training, and their causes:
Jackson Cavallerano (age 24): Running for National Braille Press to support literacy for the visually impaired
What are you up to these days? After graduating from Bryant University in 2022 I moved to Manhattan for two years and began my career in sales. I’ve since moved back to Boston and joined Toast where I am a sales associate on their small/medium business team. I’m currently living in the historic North End of Boston, which is within walking distance to Toast’s Seaport HQ. It’s been incredible not only moving back to where I was born but also being closer to family, friends, and working at one of the best tech companies in the world. I’m hoping to become a field rep in the next couple of months and continue my journey with Toast.
What’s your running background and how’s your training going? I grew up playing a lot of sports, eventually settling down with Lacrosse and Rowing mainly. There were a few times I ran track during the off season between sports but I never did much distance running. I started to get into longer distances once I started doing spartan races (up to 10k-ish range) but this will be the farthest I’ve ever gone at once. Whenever we can, we try and train together. This was easy to do when we were all home for the holidays, with my brothers making the occasional trip home and us getting some miles in. At the very least, we keep each other well informed with strategies, accomplishments, and anything else that comes up. It would be great to stick together for the race, I think we may try and do so until at least the halfway point of Wellesley Public Library — we shall see!
How have you approached fundraising? I’ve got a great support crew and network around me, they’ve really been my backbone throughout training and fundraising. I’m also grateful for Toast’s matching program and have leaned into peers and friends to help me achieve and surpass my goal. My family has also played a crucial role in supporting me both emotionally and with my fundraising efforts. I’ve got both my brothers running as well as a few other close friends so I’ll take what I can get even if it’s split between 5+ people.
Any fun or poignant stories to share re: your training, fundraising, etc. related to the marathon? Honestly it’s just been a load of fun training with friends that are big runners, practically skating along the marathon route as I took on heartbreak hill for the first time a few weekends back, and taking in my surroundings when I train throughout the city and waterfront. Even on vacation – gotta get those miles in!
Anything else worth noting? I wanted to challenge myself in multiple ways when I moved back to Boston. New job, new setup, and now running Boston in 2025. I’ve been a supporter of National Braille Press since I was born.. Going to their book fairs, beep ball games, running the vision 5k, and more recently attending Galas and golf tournaments. It’s really about creating equal opportunities for everyone, no matter what. And it’s been great to make some lifelong friends and connections along the way.
Louis Cavallerano (age 20): Friends of Wellesley Veterans to support veterans
What are you up to these days? I am currently a second year student at Bryant University, in Smithfield, RI, Studying Marketing and Political Science.
What’s your running background and how’s your training going? No official running background, I played lacrosse in high school and continued the sport at the club level at Bryant. Training is going well, considering this is my first marathon, and running is not a big hobby, I am seeing improvement in my endurance and stamina. We are sadly not training together, primarily due to location and logistics. Our running levels are slightly different but come race day, I’m confident that if we need to slow our pace down a bit, or speed up! We will be there for one another.
How have you approached fundraising? Being my first fundraiser, I’m learning things along the way. Constant communication via social media, emails, and other media types has been a great help in raising funds. Posting regular updates regarding funding and training progress allows potential donors to follow me along my journey.
Nicholas Cavallerano (age 22): Wellesley War Memorial Scholarship to support service and education
What are you up to these days? I am a Wellesley Scholarship Foundation scholar studying at the University of Rochester and this is my last semester. I’m double majoring in political science and Italian with a minor in earth sciences.
What’s your running background and how’s your training going? I played three sports throughout high school and have been training with my brothers when I am home in Wellesley. At school, I train with my friends and run around campus and indoors at the athletic center. Running in the snow and on ice is definitely an experience. I plan to stick together with my brothers during the race and finish together.
How have you approached fundraising? I have focused on my friends and family who have seen first hand how important education is to me as well as honoring veterans. I am thrilled to support and share the work of WSF and the Town’s War Memorial Scholarship.
Anything else worth noting? I just wanted to thank the Bank of America, the Boston Athletic Association, the Wellesley Select Board, and especially Stephanie Hawkinson for organizing the town’s annual charity marathon program. It’s a wonderful opportunity for me and other residents to give back to a community and the great local charities that have given so much to so many. It’s an honor to be part of this effort.
More: Wellesley’s 2025 Boston Marathon charity runners
