| 2017 | $0.00 | PMC Rider |
| 2016 | $7,795.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $16,710.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $10,000.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $9,645.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $13,185.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $5,125.00 | Sturbridge to Provincetown Monument (2-Day) |
