| 2022 | $6,025.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $0.00 | PMC Rider |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
