| 2021 | $9,000.00 | Reimagined |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,650.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $11,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,770.00 | Wellesley to Provincetown Inn (2-Day) |
