| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $0.00 | PMC Rider |
| 2015 | $500.00 | PMC Rider |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
