| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| $0.00 | PMC Unpaved | |
| 2023 | $4,100.21 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $4,000.16 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $644.62 | Wellesley to Bourne (1-Day, Sat) |
