| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $10,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $3,775.00 | Reimagined |
| 2022 | $5,170.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $3,980.00 | Reimagined |
| 2020 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $8,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,375.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,725.00 | Wellesley to Bourne (1-Day, Sat) |
