| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $2,320.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $3,630.00 | Wellesley Century |
| 2021 | $4,097.10 | Wellesley Century |
| 2020 | $190.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,615.30 | Sturbridge to Provincetown Monument (2-Day) |
