| 2025 | $300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $17,253.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $13,058.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $11,449.00 | Sturbridge to Provincetown Monument (2-Day) |
