| 2024 | $0.00 | PMC |
| 2022 | $8,100.00 | Reimagined |
| 2020 | $6,564.40 | PMC Rider |
| 2019 | $5,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $7,446.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,890.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $250.00 | PMC Rider |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,340.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,331.00 | Sturbridge to Provincetown Inn (2-Day) |
