| Russell Hallisey | $100.00 |
| 2025 | $11,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,057.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $14,400.00 | Reimagined |
| 2022 | $10,275.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,100.00 | Reimagined |
| 2020 | $10,139.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $12,923.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,375.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,479.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $12,007.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $11,653.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,430.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,332.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Wellesley (2-Day) |
| 2011 | $4,786.41 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $5,547.16 | Wellesley to Provincetown Monument (2-Day) |
| 2009 | $3,625.00 | Sturbridge to Wellesley (2-Day) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $6,304.93 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $7,195.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,325.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,505.66 | Sturbridge to Wellesley (2-Day) |
| 2002 | $4,729.50 | Wellesley to Wellesley (2-Day) |
