| 2025 | $7,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $28,239.24 | Sturbridge to Provincetown Monument (2-Day) |
| $1,910.00 | PMC Unpaved | |
| 2023 | $25,630.89 | Sturbridge to Provincetown Monument (2-Day) |
| $1,600.00 | PMC Unpaved | |
| 2022 | $24,335.31 | Sturbridge to Provincetown Monument (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2021 | $21,144.89 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $15,471.89 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,818.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $8,012.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,810.68 | Sturbridge to Wellesley (2-Day) |
| 2016 | $9,200.00 | Sturbridge to Wellesley (2-Day) |
| 2015 | $7,384.55 | Sturbridge to Wellesley (2-Day) |
| 2014 | $7,070.00 | Sturbridge to Wellesley (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Wellesley (2-Day) |
| 2012 | $6,955.00 | Sturbridge to Wellesley (2-Day) |
| 2011 | $6,945.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $12,715.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $0.00 | PMC |
| 2006 | $4,770.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $6,040.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $4,627.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,320.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,720.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,205.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $1,000.00 | PMC Rider |
| 1996 | $1,000.00 | PMC Rider |
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