| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $7,507.94 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $0.00 | Virtual Ride |
| $8,767.00 | PMC Unpaved | |
| 2022 | $8,419.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,560.00 | Wellesley Century |
| 2020 | $6,010.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,262.25 | Wellesley to Wellesley (2-Day) |
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