| Richard Testa | $50.00 |
| 2025 | $50.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,126.27 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,128.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 1998 | $1,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $1,000.00 | PMC Rider |
