| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,416.82 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,687.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $7,033.70 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,446.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $3,441.00 | Wellesley to Bourne (1-Day, Sat) |
