| 2025 | $100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $4,100.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,550.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,125.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $0.00 | PMC Rider |
| 2017 | $4,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $0.00 | PMC Rider |
| 2015 | $4,200.00 | Wellesley to Wellesley (2-Day) |
| 2014 | $3,500.00 | Sturbridge to Wellesley (2-Day) |
| 2013 | $3,500.00 | Sturbridge to Wellesley (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $3,400.00 | Sturbridge to Wellesley (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,000.00 | Sturbridge to Wellesley (2-Day) |
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