| 2025 | $100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $11,563.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,569.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,193.86 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2021 | $12,767.84 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $14,377.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,758.81 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $11,735.87 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,240.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $12,235.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $9,048.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $8,288.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,678.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,998.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,553.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,604.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,065.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,380.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,615.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,495.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,925.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $4,185.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $4,426.40 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $3,540.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,550.00 | PMC Rider |
| 1996 | $2,000.00 | PMC Rider |
| 1995 | $2,000.00 | PMC Rider |
