| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $9,357.76 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,826.52 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $13,939.10 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $240.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $15,942.56 | Wellesley to Bourne (1-Day, Sat) |
