| 2025 | $3,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $7,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $2,000.00 | Reimagined |
| 2019 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $6,950.76 | Wellesley to Bourne (1-Day, Sat) |
