| 2021 | $5,670.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2015 | $4,283.33 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $3,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $3,225.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $3,100.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $4,255.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $3,875.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $2,300.00 | Wellesley to Bourne (1-Day, Sat) |
