| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $90.00 | PMC Rider |
| 2013 | $4,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,225.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,318.00 | Sturbridge to Provincetown Inn (2-Day) |
