| 2021 | $2,000.00 | Reimagined |
| 2020 | $1,905.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,655.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,021.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,658.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,624.42 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,301.00 | Sturbridge to Provincetown Monument (2-Day) |
