| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,226.07 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,795.22 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,718.30 | Reimagined |
| 2020 | $1,513.00 | PMC Rider |
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