| 2017 | $5,345.16 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $0.00 | PMC Rider |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,440.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
