| 2024 | $9,520.80 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $9,053.56 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,305.55 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,125.00 | Wellesley Century |
| 2020 | $7,475.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,175.63 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,795.61 | Sturbridge to Bourne (1-Day, Sat) |
| 2017 | $10,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,325.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $9,615.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $400.00 | PMC Rider |
| 2013 | $7,445.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,995.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $8,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $8,203.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,785.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $10,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $7,685.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,625.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $4,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $3,085.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,680.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,522.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,809.00 | Sturbridge to Provincetown Inn (2-Day) |
