| Peter Sacks | $100.00 |
| 2025 | $100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,060.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,060.00 | Sturbridge to Bourne + Wellesley Century (2-Day) |
| 2021 | $6,033.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $2,418.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $6,210.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,054.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $4,650.00 | Wellesley to Bourne (1-Day, Sat) |
