| Laurie and Peter Quimby | $250.00 |
| 2025 | $4,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $3,250.00 | Wellesley Century |
| 2022 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $3,200.00 | Wellesley Century |
| 2020 | $3,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,275.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,000.00 | Sturbridge to Bourne (1-Day, Sat) |
