| 2024 | $5,060.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2023 | $11,960.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $7,505.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $4,021.00 | Wellesley Century |
| 2020 | $3,140.61 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,175.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
