| 2021 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $50.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $1,250.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,680.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $50.00 | PMC Rider |
| 2014 | $1,140.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $1,025.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2012 | $1,000.00 | Wellesley to Patriot Place (25 mile Sunday) |
