| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,390.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,608.72 | Sturbridge to Provincetown Monument (2-Day) |
