| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,157.82 | Wellesley Century |
| 2020 | $1,696.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,625.90 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $1,015.00 | Wellesley to Wellesley (50 mile Sunday) |
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