| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2020 | $75.00 | 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 | $4,500.40 | Sturbridge to Provincetown Inn (2-Day) |
