| 2024 | $6,097.10 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $4,678.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $160.00 | Sturbridge to Provincetown Monument (2-Day) |
