| 2023 | $6,122.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Reimagined |
| 2020 | $2,146.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,479.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2018 | $5,193.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,282.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,430.92 | Sturbridge to Provincetown Inn (2-Day) |
