| 2021 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $290.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,045.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,215.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,355.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,395.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,699.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $3,820.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $6,107.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,140.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,425.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,240.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $6,690.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,590.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,833.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,415.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,921.52 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,819.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,998.40 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $1,051.40 | PMC Rider |
| 1995 | $1,090.82 | PMC Rider |
| 1994 | $1,037.40 | PMC Rider |
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