| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,238.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $4,258.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,011.70 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $3,830.00 | Wellesley Century |
| 2020 | $625.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $4,058.95 | Wellesley to Bourne (1-Day, Sat) |
