| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $33,247.25 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $28,105.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $22,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $21,231.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $17,438.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $16,864.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $14,385.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $14,710.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $18,049.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $11,640.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $11,385.89 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $11,636.09 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $8,060.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $6,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $6,401.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $6,155.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $6,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $6,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $6,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2005 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,705.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $5,180.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $4,940.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $4,895.47 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,545.00 | Wellesley to Provincetown Inn (2-Day) |
| 1998 | $1,488.00 | Wellesley to Provincetown Inn (2-Day) |
| 1997 | $1,015.00 | PMC Rider |
