| 2022 | $6,477.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,609.80 | Reimagined |
| 2020 | $3,073.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,728.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,337.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $5,477.65 | Sturbridge to Provincetown Inn (2-Day) |
