| 2025 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,100.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
