The 2026 Chappy Point to Point Road Race took place on Sunday, June 28, on beautiful Chappaquiddick Island. This five-mile point-to-point race, beginning near Wasque Point and finishing at the Chappy Ferry, is the longest continually running road race on Martha’s Vineyard. With a field limited to 340 participants, the race has maintained the intimate, community-oriented atmosphere that makes it so special. Runners and walkers gathered early in the morning at the Chappy Ferry parking area before being transported to the starting line. From there, participants made their way across the island toward the ferry, enjoying the unique landscape and character of Chappaquiddick along the way. The race is as much about the experience as it is about competition, bringing together serious runners, recreational runners, walkers, local residents, and visitors for a memorable summer morning. An especially meaningful part of the 2026 event was its charitable mission. Race proceeds supported Chappy Connect, a transportation service for Chappaquiddick residents age 60 and older. Through the Edgartown Council on Aging and Healthy Aging MV, Chappy Connect provides free, pre-scheduled transportation to important destinations such as grocery stores, pharmacies, medical appointments, and the Steamship Authority.
What makes the Chappy Point to Point particularly enjoyable is its combination of tradition, scenery, community, and giving back. Unlike larger road races, the event does not feel commercial or overwhelming; instead, it captures the relaxed spirit of Chappaquiddick and Martha’s Vineyard. The ferry, the small field, the beautiful island roads, and the point-to-point format all contribute to an experience that participants remember long after crossing the finish line. Knowing that the race also helps support transportation for older Chappy residents adds another important dimension to the event. The 2026 race once again showed why this tradition has remained such an important part of the island’s summer running calendar. Whether participants were racing for a personal best, enjoying a run with friends, or simply taking in the scenery, everyone shared the same five-mile journey from Wasque Point to the Chappy Ferry while contributing to a cause that directly benefits the local community. In the end, the Chappy Point to Point is more than just a road race—it is a celebration of Chappaquiddick, community, tradition, and the simple pleasure of being outside together while giving something back.
