| 2023 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $1,090.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Provincetown Inn (2-Day) |
