| William Riggieri | $60.00 |
| Matthew Palmisano | $120.00 |
| 2025 | $180.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $10,000.26 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $7,885.03 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,694.10 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,071.03 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
