| Ricardo Overeem | $30.00 |
| Jack O’Reilly | $30.00 |
| Tyler Reid |
| 2025 | $210.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Bourne to Provincetown Inn (1-Day, Sun) |
