| 2019 | $2,920.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $4,050.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $1,250.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $4,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $2,150.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $3,012.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $5,420.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $3,055.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2007 | $6,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $6,000.00 | Sturbridge to Bourne (1-Day, Sat) |
