| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,611.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,170.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $4,135.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $1,080.00 | PMC Rider |
| 2019 | $5,251.69 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,490.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $5,264.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $4,780.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,950.00 | Sturbridge to Provincetown Inn (2-Day) |
