| 2019 | $5,004.80 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $5,090.84 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,200.12 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,950.00 | Wellesley to Provincetown Monument (2-Day) |
