If you wrote a list of the most important characters in the story of Martha’s Vineyard, it would have to include Moshup, Bartholomew Gosnold, and Ronald Rappaport. Moshup shaped the Island, Gosnold named it, and Ron took care of it. But this is not a story about Moshup’s whales, or Gosnold’s daughters. This is not even a story about how Ronald dedicated much of his life to keeping the Island running smoothly. It’s a story so true and genuine I feel inadequate to be the one sharing it. This story’s about Ron’s love for bicycles.
For many of his 74 years, the roads and bike paths of Martha’s Vineyard, winding from his home on Lucy Vincent to his office in Edgartown, were lined with Ron’s bike tracks. Whether with friends or alone, Ron was easy to spot, with his Einstein-esque hair. Jim Reynolds, Ron’s longtime law partner, remembers Ron as “an amazing sight on a bicycle, with the hair and the helmet just kind of perched on top.”
Ron’s life on a bike went back to his childhood. Ron rode his bike to the Oak Bluffs School and home, alongside his sister, Susan Cohen, and best friend, Dennis daRosa. Ron moved away, but he and his wife, Jane Kaplan, would come on summer weekends. Over time they worked their mileage up to the point they could ride from the Island Queen to Aquinnah and back in a day. When he and his brother Alan began riding the Pan Mass Challenge, a fundraising ride for Dana-Farber Cancer Institute, Ron got serious about cycling. Jane remembers that he was gifted a fancy bike, and “became utterly infatuated.”
After he moved back to the Island full-time, Ron rode to work every day he could. Jim tells of Ron persuading the other building owners to install an outdoor shower: “Ron would ride in wearing his bike stuff, shower outside, and jump into his work clothes, then reverse the process at the end of the day.” When Ron’s grandson, Sam, turned 3 years old, Ron and Jane gave him his first two-wheeler bike — no training wheels. Sam shared his grandfather’s passion and talent, and was peddling away two days later.
With one hand on the handlebars, Ron always had his other hand in the Island community. Since Ron’s passing in June 2024, countless stories have been shared of his important and irreplaceable involvement in everything from the Steamship ferries that bring us here to the college scholarships that propel us away. It would be hard to find an Island organization that didn’t benefit from the wisdom of Ronald Rappaport.
In 2020, after six months of COVID lockdown, Kerry Alley reached out to Ron on behalf of the Red Stocking Fund, worried that they were short of their fundraising goals due to the pandemic. Ronald agreed to help, and raised more than $100,000 for the Red Stocking Fund, ensuring holiday presents, clothes, and food for Island children in need that year, and for the following years.
The Red Stocking Fund uses monetary donations to buy clothing, while toy drives and targeted donations ensure all the children receive books, puzzles, and art and school supplies, as well as extra-special presents when possible.
Sandy Joyce, co-chair of Red Stocking, says, “Every year, bikes are the most requested item, and we have never been able to meet all the requests.”
This year, there was an anonymous donation in Ronald Rappaport’s honor. In addition to other winter needs, the money received funded 49 extra bikes, and Red Stocking was able to give a bike to every child who wanted one.
Fellow Red Stocking co-chair Susie Wallo said, “The Martha’s Vineyard community both near and far have made the magic happen for our children in need every year since 1938. Due to an anonymous benefactor and a few other local businesses, every child who asked for a bicycle from Santa was able to get their Christmas wish answered.”
This coming spring, and for years to come, children will be riding “Ron’s Bikes” to the beach, to school, and summer jobs, and carrying on Ron’s love of nature, cycling, and his commitment to Vineyard youth. Julia Rappaport reflects on this donation, a combination of her father’s passion for supporting Island youth, and his passion for pedals:
“For so long, Dad supported the Red Stocking Fund through personal donations and behind-the-scenes efforts. This incredible gesture is full circle. With it, Red Stocking is supporting our family in carrying Dad’s legacy forward. What a gift.”
