| Rebecca Hubbard | $50.00 |
| Vasilii Trombly |
| 2025 | $100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,549.76 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,908.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,909.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,724.60 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $673.00 | Sturbridge to Provincetown Inn (2-Day) |
