| 2022 | $4,625.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $2,501.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Inn (2-Day) |
