| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2020 | $125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,681.00 | Sturbridge to Provincetown Inn (2-Day) |
