| 2020 | $2,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,410.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $6,220.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $6,285.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $6,875.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $5,095.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,705.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,325.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $1,526.67 | Wellesley to Wellesley (50 mile Sunday) |
| 2007 | $1,283.50 | Wellesley to Wellesley (50 mile Sunday) |
