| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $10,253.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $5,300.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $7,023.68 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,135.00 | Wellesley to Bourne (1-Day, Sat) |
