| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,836.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $5,285.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $115.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $5,200.00 | Wellesley to Provincetown Monument (2-Day) |
