| 2025 | $0.00 | PMC |
| 2024 | $6,795.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $8,275.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,725.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $4,270.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,165.00 | Sturbridge to Provincetown Monument (2-Day) |
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