| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $2,601.89 | Reimagined |
| 2023 | $2,885.00 | Reimagined |
| 2022 | $3,950.00 | Reimagined |
| 2021 | $7,975.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,145.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,050.00 | Sturbridge to Provincetown Monument (2-Day) |
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