| 2017 | $0.00 | PMC Rider |
| 2016 | $30.00 | PMC Rider |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,970.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,320.00 | Sturbridge to Wellesley (2-Day) |
| 2011 | $4,795.00 | Sturbridge to Provincetown Inn (2-Day) |
