| 2025 | $350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $20,030.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $14,620.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $16,780.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $17,086.00 | Reimagined |
| 2020 | $26,560.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $30,770.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $24,262.81 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $20,887.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $25,949.26 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $24,241.38 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $22,242.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $20,425.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $18,495.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $20,813.31 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $12,861.00 | Sturbridge to Provincetown Monument (2-Day) |
