| 2022 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $6,916.00 | Reimagined |
| 2020 | $3,090.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,042.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,520.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,199.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $5,932.63 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $5,230.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $5,547.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,561.43 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
