| 2016 | $0.00 | PMC Rider |
| 2015 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $6,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,600.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,300.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
