| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $17,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $22,775.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $20,768.55 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $12,655.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $14,685.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $15,000.00 | Sturbridge to Provincetown Monument (2-Day) |
