| 2025 | $0.00 | PMC Unpaved |
| 2024 | $7,570.49 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $4,000.00 | PMC Unpaved |
| 2022 | $7,257.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $5,255.00 | Reimagined |
| 2020 | $5,101.00 | Sturbridge to Provincetown Monument (2-Day) |
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