| 2019 | $5,070.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.84 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $1,380.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $1,050.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $7,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
