| 2020 | $1,600.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,830.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,405.00 | Sturbridge to Provincetown Monument (2-Day) |
| $500.00 | PMC Winter Cycle | |
| 2017 | $4,802.25 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | The Resolution by PMC | |
| 2015 | $5,681.99 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $5,240.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,646.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $12,342.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
