| 2024 | $6,145.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $1,150.00 | Virtual Ride |
| 2021 | $1,075.00 | PMC Rider |
| 2020 | $1,110.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,020.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,450.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $5,530.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,038.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $5,850.56 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $4,670.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,955.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,272.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $5,590.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $3,690.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,678.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,082.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $5,310.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1990 | $1,266.00 | PMC Rider |
| 1989 | $1,244.00 | PMC Rider |
| 1988 | $1,372.00 | PMC Rider |
| 1987 | $1,236.00 | PMC Rider |
| 1986 | $1,109.00 | PMC Rider |
| 1985 | $701.00 | PMC Rider |
| 1984 | $642.00 | PMC Rider |
| 1983 | $397.00 | PMC Rider |
| 1982 | $358.00 | PMC Rider |
| 1981 | $100.00 | PMC Rider |
