| 2020 | $325.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $8,020.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $11,600.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $11,069.08 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $6,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,685.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $7,740.83 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $3,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2005 | $3,105.45 | Sturbridge to Provincetown Inn (2-Day) |
