| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,045.52 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,980.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,415.00 | Reimagined |
| 2020 | $5,387.70 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,191.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $9,234.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $9,121.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,890.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,426.68 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,590.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,700.38 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,889.62 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $9,788.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $8,065.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $4,673.23 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,502.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,440.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,713.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,030.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,625.00 | Sturbridge to Provincetown Inn (2-Day) |
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