| 2024 | $10,580.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $356.48 | PMC Fundraiser |
| 2022 | $12,102.05 | Virtual Ride |
| 2021 | $17,478.26 | Virtual Ride |
| 2020 | $11,780.64 | PMC Rider |
| 2019 | $13,227.43 | PMC Rider |
| 2018 | $12,313.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $12,427.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $11,837.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $12,275.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $9,493.04 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $8,164.59 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,003.31 | PMC Rider |
| 2011 | $6,577.84 | PMC Rider |
| 2010 | $6,875.00 | PMC Rider |
| 2009 | $9,284.86 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $9,520.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $10,021.31 | Wellesley to Wellesley (2-Day) |
| 2006 | $16,000.00 | Wellesley to Wellesley (2-Day) |
| 2005 | $8,010.92 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $12,344.09 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $24,631.90 | Sturbridge to Provincetown Inn (2-Day) |
