| 2013 | $50.00 | PMC Rider |
| 2012 | $50.00 | PMC Rider |
| 2011 | $3,043.61 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $3,281.42 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $3,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $4,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2007 | $3,080.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2006 | $3,525.00 | Wellesley to Provincetown Monument (2-Day) |
