| 2023 | $50.00 | PMC Fundraiser |
| 2022 | $75.00 | PMC Fundraiser |
| 2020 | $785.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $0.00 | PMC Rider |
| 2015 | $50.00 | PMC Rider |
| 2014 | $420.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $0.00 | PMC Rider |
| 2012 | $2,675.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,450.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $5,316.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $4,130.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $2,605.00 | Sturbridge to Bourne (1-Day, Sat) |
