| 2025 | $0.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2024 | $2,000.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $2,050.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2022 | $2,000.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2021 | $5,399.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $4,089.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $3,175.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $4,870.00 | Sturbridge to Provincetown Monument (2-Day) |
