| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $2,029.91 | Reimagined |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $1,365.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,655.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,316.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,135.00 | Sturbridge to Provincetown Inn (2-Day) |
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