| Austin Murphy | $500.00 |
| 2025 | $500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2023 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,000.00 | Sturbridge to Provincetown Monument (2-Day) |
