Ronald Rappaport's life on Martha’s Vineyard was marked by his profound love for cycling and his unwavering dedication to the community. For many years, Ron's bicycle tracks were a familiar sight on the island's winding roads and paths. His passion for cycling began in childhood and grew into a lifelong commitment that intertwined with his efforts to support local organizations. After his passing in June 2024, countless stories emerged about his significant contributions, especially to the Red Stocking Fund, which provides essential items for children in need. In his honor, an anonymous donation funded 49 additional bicycles, ensuring every child who wished for one received it. This gesture not only honored Ron's legacy but also carried forward his deep-rooted love for cycling and youth development.

A Life Pedaled Through Passion

Ronald Rappaport's connection to Martha’s Vineyard was deeply rooted in his love for cycling. From childhood rides through Oak Bluffs to daily commutes from Lucy Vincent to Edgartown, Ron's bike became an extension of himself. Friends remember him as an "amazing sight" on two wheels, with his distinctive hairstyle adding to the charm. Ron's cycling journey evolved over the years, from casual rides with family and friends to more serious endeavors like the Pan Mass Challenge, a fundraising event for cancer research. His enthusiasm for cycling was infectious, inspiring others, including his grandson Sam, who learned to ride without training wheels at just three years old. Ron's commitment to cycling was not just a personal passion but a way of life that reflected his zest for adventure and community involvement.

Throughout his life, Ron's bike was his constant companion. He cycled to school as a child, rode alongside his sister Susan and best friend Dennis during their formative years, and continued this tradition well into adulthood. When he returned to Martha’s Vineyard full-time, Ron made cycling a part of his daily routine, riding to work whenever possible. His colleagues recall how he would arrive in cycling gear, shower outside, and change into work clothes—a testament to his dedication. Ron's love for cycling extended beyond personal enjoyment; it symbolized his deep connection to nature and the island's beauty. His passion for biking was not just a hobby but a reflection of his values and lifestyle. Whether pedaling solo or with companions, Ron's presence on the island's roads was a reminder of his enduring spirit and love for the community.

An Unbreakable Bond with the Community

Beyond his cycling pursuits, Ronald Rappaport was an integral part of Martha’s Vineyard's community fabric. His contributions touched nearly every aspect of island life, from transportation services to educational scholarships. One of his most notable involvements was with the Red Stocking Fund, a charitable organization dedicated to providing essentials for children in need. During the pandemic, Ron stepped up to help the fund meet its fundraising goals, raising over $100,000 to ensure holiday gifts, clothing, and food for local children. His generosity and leadership ensured that the Red Stocking Fund could continue its mission, even in challenging times. The impact of his efforts was felt far and wide, with numerous children benefiting from his support.

After Ron's passing, the community rallied to honor his memory. An anonymous donation in his name provided 49 additional bicycles, fulfilling every child's wish for a bike. This act of kindness not only honored Ron's legacy but also carried forward his commitment to supporting youth and fostering a sense of belonging. Fellow Red Stocking co-chair Susie Wallo highlighted the significance of this donation, stating that it allowed the organization to fulfill all bicycle requests for the first time. Ron's daughter Julia reflected on this gesture, noting that it was a fitting tribute to her father's lifelong dedication to the island's youth and his passion for cycling. Through these bikes, children will carry on Ron's love for nature, cycling, and community service, ensuring that his legacy lives on for generations to come.