| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $8,588.47 | Wellesley to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2023 | $10,140.00 | Wellesley to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2022 | $9,625.00 | Wellesley to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2021 | $12,604.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $535.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,370.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,365.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,880.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,475.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $2,200.00 | Sturbridge to Wellesley (2-Day) |
| 2004 | $2,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $3,095.00 | Sturbridge to Provincetown Inn (2-Day) |
