| 2024 | $0.00 | PMC |
| $15,397.23 | PMC Unpaved | |
| 2021 | $0.00 | PMC Rider |
| 2020 | $24,415.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $15,809.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $12,204.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,408.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $18,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $16,062.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $14,150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $11,171.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $9,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,904.00 | Sturbridge to Provincetown Monument (2-Day) |
