| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $306.67 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,900.76 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,562.50 | Sturbridge to Provincetown Monument (2-Day) |
