| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $8,152.25 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,017.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $8,409.11 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $4,997.00 | Patriot Place to Patriot Place |
| 2020 | $3,795.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,108.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,350.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $8,155.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,605.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $1,929.00 | Wellesley to Wellesley (50 mile Sunday) |
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