| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,518.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,429.90 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,616.25 | Sturbridge to Provincetown Inn (2-Day) |
