| 2025 | $0.00 | PMC Unpaved |
| 2024 | $4,630.00 | PMC Unpaved |
| 2022 | $8,945.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $7,230.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,480.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,927.76 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,342.76 | Sturbridge to Provincetown Inn (2-Day) |
