| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $9,139.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $9,160.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,461.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,778.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $4,779.99 | Bourne to Wellesley (1-Day, Sun) |
| 2019 | $6,071.07 | Wellesley to Provincetown Inn (2-Day) |
