| 2016 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $6,260.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $6,903.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,082.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $6,655.00 | Wellesley to Bourne (1-Day, Sat) |
