| Andrew Clurman | $6,000.00 |
| Andrew Clurman | $6,000.00 |
| 2025 | $12,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,650.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $20.00 | Sturbridge to Provincetown Inn (2-Day) |
