| 2025 | $350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $17,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,555.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,220.00 | Reimagined |
| 2020 | $3,826.28 | Sturbridge to Bourne (1-Day, Sat) |
| 2019 | $5,060.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,049.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,804.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,736.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,015.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,031.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $8,411.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,405.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,175.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $9,446.00 | Wellesley to Provincetown Monument (2-Day) |
