| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,666.03 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,677.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,035.35 | Reimagined |
| 2020 | $5,501.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,726.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,661.00 | Sturbridge to Provincetown Monument (2-Day) |
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