| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,158.92 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $0.00 | PMC Rider |
| 2016 | $25.00 | PMC Rider |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
