| Ted Diamond | $108.00 |
| Daniel Lieber |
| 2025 | $133.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $12,207.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $13,748.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $23,185.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $10,073.00 | Wellesley Century |
| 2020 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $10,894.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,129.00 | Wellesley to Bourne (1-Day, Sat) |
