| 2019 | $5,250.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $3,352.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $7,800.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $1,565.00 | PMC Virtual Rider and Volunteer |
| 2015 | $7,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Bourne (1-Day, Sat) |
