| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $21,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $27,350.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $13,955.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $7,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $6,200.00 | Wellesley to Wellesley Teens (50 mile Sunday) |
| 2019 | $5,900.00 | Wellesley to Patriot Place Teens (25 mile Sun) |
