| Joel Feinberg | $5,000.00 |
| 2025 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,844.75 | Wellesley to Provincetown Monument (2-Day) |
| $0.00 | PMC Unpaved | |
| 2020 | $2,665.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
