| 2023 | $0.00 | PMC |
| 2022 | $4,060.00 | Reimagined |
| 2021 | $4,458.26 | Reimagined |
| 2020 | $2,041.00 | PMC Rider |
| 2019 | $2,355.00 | PMC Rider |
| 2018 | $1,685.00 | PMC Rider |
| 2014 | $4,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $1,930.00 | Bourne to Wellesley (1-Day Sun) and Volunteer |
| 2012 | $4,423.00 | Sturbridge to Provincetown Monument (2-Day) |
