| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $8,615.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,395.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,300.00 | Reimagined |
| 2021 | $20,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $18,389.75 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $19,061.13 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $20,059.85 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $12,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $20,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,523.42 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,927.32 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $9,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $10,230.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $7,535.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,570.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,710.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,920.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,432.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $1,110.00 | PMC Rider |
