| John Buchta | $1,000.00 |
| 2025 | $1,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $13,312.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,861.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $32,890.65 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $0.00 | PMC Rider |
