| 2024 | $4,411.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $10,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,025.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $7,625.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $10,365.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,331.00 | Wellesley to Provincetown Inn (2-Day) |
