| 2022 | $8,890.86 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $25.00 | PMC Rider |
| 2016 | $50.00 | PMC Rider |
| 2015 | $7,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $50.00 | PMC Rider |
| 2013 | $6,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,122.13 | Sturbridge to Bourne (1-Day, Sat) |
| 2008 | $3,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2007 | $3,100.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2005 | $2,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2004 | $1,750.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2003 | $1,507.00 | Sturbridge to Bourne (1-Day, Sat) |
