| 2020 | $140.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,305.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,950.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
