| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,000.22 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,761.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,216.35 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $5,259.80 | Reimagined |
| 2020 | $891.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,287.70 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,845.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,875.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,775.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,337.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $5,085.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,456.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,250.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,200.96 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $4,265.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $3,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,400.00 | Wellesley to Provincetown Inn (2-Day) |
