| 2019 | $125.00 | PMC Rider |
| 2018 | $120.00 | PMC Rider |
| 2017 | $8,080.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,568.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,236.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $9,013.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $11,517.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $9,144.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $8,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $7,659.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,267.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,761.00 | Sturbridge to Provincetown Inn (2-Day) |
