| 2025 | $0.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2024 | $3,250.02 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $2,064.00 | Virtual Ride |
| 2022 | $2,500.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2021 | $2,500.00 | Patriot Place to Wellesley |
| 2020 | $1,500.00 | Wellesley to Patriot Place (25 mile Sunday) |
