| 2024 | $350.00 | PMC Virtual Rider |
| 2023 | $10,001.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $150.00 | Virtual Ride |
| 2021 | $510.00 | Virtual Ride |
| 2020 | $75.00 | PMC Rider |
| 2019 | $250.00 | PMC Rider |
| 2018 | $200.00 | PMC Rider |
| 2017 | $235.00 | PMC Rider |
| 2016 | $150.00 | PMC Rider |
| 2015 | $3,800.68 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $7,093.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,910.00 | PMC Rider |
| 2012 | $6,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,630.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $6,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $6,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,328.34 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $9,663.63 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $10,182.00 | Wellesley to Bourne (1-Day, Sat) |
