| 2024 | $0.00 | PMC |
| $5,945.00 | PMC Unpaved | |
| 2023 | $18,457.50 | Sturbridge to Provincetown Monument (2-Day) |
| $5,313.28 | PMC Unpaved | |
| 2022 | $14,665.00 | Sturbridge to Provincetown Monument (2-Day) |
| $3,000.00 | PMC Unpaved | |
| 2021 | $14,421.68 | Reimagined |
| 2020 | $20,777.10 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $13,527.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $14,829.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $13,591.31 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $13,947.75 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $11,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $11,669.08 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $6,650.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $6,950.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $7,370.83 | Sturbridge to Provincetown Monument (2-Day) |
