| 2020 | $3,942.25 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $7,325.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,580.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,595.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $10,020.00 | Sturbridge to Provincetown Monument (2-Day) |
