| 2022 | $6,000.00 | Reimagined |
| 2021 | $7,015.50 | Wellesley Century |
| 2020 | $6,080.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,633.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,200.00 | Wellesley to Provincetown Inn (2-Day) |
