| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,407.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,921.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,515.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $0.00 | Virtual Ride |
| 2020 | $1,000.00 | PMC Rider |
| 2019 | $5,667.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,720.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
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