| 2024 | $0.00 | PMC |
| $4,608.41 | PMC Unpaved | |
| 2023 | $6,194.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,511.95 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2021 | $3,365.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $2,980.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,095.00 | Sturbridge to Provincetown Inn (2-Day) |
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