| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $11,787.75 | Wellesley to Provincetown Monument (2-Day) |
| $4,500.00 | PMC Unpaved | |
| 2023 | $10,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,060.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $9,003.00 | Wellesley Century |
| 2020 | $5,040.00 | Wellesley to Bourne (1-Day, Sat) |
