| 2025 | $200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,123.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $11,234.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,032.81 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,620.36 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,890.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,696.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,854.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,509.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,247.81 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $6,950.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,825.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,508.33 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $6,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $6,785.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $6,046.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $6,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $8,592.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $4,096.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2005 | $7,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2004 | $6,590.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $6,705.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $6,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $5,875.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $5,155.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $2,839.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1996 | $1,460.00 | PMC Rider |
