| 2018 | $4,900.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,490.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $4,749.00 | Wellesley to Provincetown Monument (2-Day) |
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