| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,272.10 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,696.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,947.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,150.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $1,362.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,256.14 | Wellesley to Provincetown Monument (2-Day) |
