| 2021 | $6,000.00 | Wellesley Century |
| 2020 | $6,790.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,905.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $9,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,275.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $6,020.62 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $6,525.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $6,947.25 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $4,975.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,825.00 | Sturbridge to Provincetown Inn (2-Day) |
