| Taylor Jubanowsky | $30.00 |
| Shawn Hils | $150.00 |
| 2025 | $180.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,775.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $12,375.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,529.90 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $12,392.50 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,063.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,451.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,282.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,058.16 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $6,756.59 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $8,578.47 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $7,089.49 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $7,190.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $7,943.00 | Wellesley to Provincetown Monument (2-Day) |
