| 2023 | $2,180.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $570.00 | Virtual Ride |
| 2021 | $2,220.00 | Reimagined |
| 2020 | $800.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,835.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,430.00 | Wellesley to Patriot Place (25 mile Sunday) |
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