| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,620.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,260.00 | Reimagined |
| 2021 | $2,714.70 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $3,320.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $1,190.50 | Wellesley to Wellesley (50 mile Sunday) |
