| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $17,660.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $19,524.29 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $31,070.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $30,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $12,402.87 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $27,902.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $30,664.30 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $22,782.36 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $16,900.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $5,670.00 | Wellesley to Provincetown Monument (2-Day) |
