| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,134.59 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,271.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,980.50 | Sturbridge to Provincetown Inn (2-Day) |
| $10.00 | PMC Unpaved | |
| 2021 | $3,000.00 | Reimagined |
| 2020 | $340.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Monument (2-Day) |
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