| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,658.70 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,519.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,120.00 | Reimagined |
| 2020 | $12,507.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,661.36 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,518.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,714.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,060.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,475.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,765.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,805.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,145.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,840.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,255.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,145.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $3,095.00 | Sturbridge to Wellesley (2-Day) |
