| 2021 | $2,250.00 | Reimagined |
| 2020 | $2,240.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,235.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,907.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,815.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,639.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
