| 2021 | $4,430.00 | Reimagined |
| 2020 | $3,558.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,525.00 | Sturbridge to Provincetown Monument (2-Day) |
