| Spencer Betts | $50.00 |
| Giorgio Sarkis | $100.00 |
| 2025 | $150.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $2,110.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,783.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,694.00 | Wellesley to Wellesley (50 mile Sunday) |
