| 2025 | $11,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $7,107.55 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,045.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $165.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,800.00 | Sturbridge to Provincetown Inn (2-Day) |
