| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,000.00 | Reimagined |
| 2020 | $55.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,440.00 | Wellesley to Provincetown Monument (2-Day) |
