| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $7,020.00 | Wellesley to Provincetown Monument (2-Day) |
| $600.00 | PMC Winter Cycle | |
| 2021 | $9,357.00 | Wellesley to Bourne (1-Day, Sat) |
