| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $14,240.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $15,226.44 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $15,015.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $11,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $5,400.00 | Wellesley to Bourne (1-Day, Sat) |
