| 2022 | $6,002.55 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $3,040.00 | Wellesley Century |
| 2020 | $120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,411.33 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,127.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
