| 2021 | $2,037.00 | Reimagined |
| 2020 | $220.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,158.00 | Wellesley to Bourne (1-Day, Sat) |
