| 2025 | $0.00 | Reimagined |
| 2024 | $12,350.00 | Reimagined |
| 2023 | $10,900.00 | Reimagined |
| 2022 | $10,525.00 | Reimagined |
| 2021 | $9,400.00 | Reimagined |
| 2020 | $5,475.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,275.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,880.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,525.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,713.01 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $7,695.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $8,044.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $7,449.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $5,071.00 | Sturbridge to Provincetown Inn (2-Day) |
