| 2022 | $6,000.22 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,154.40 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $1,970.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,116.22 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,454.44 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $9,255.76 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $0.00 | PMC Rider |
| 2014 | $10.00 | PMC Rider |
| 2013 | $5,015.00 | Wellesley to Provincetown Monument (2-Day) |
