| 2025 | $0.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $17,502.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $17,890.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $16,006.50 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2021 | $26,681.12 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $10,332.83 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2019 | $12,300.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $9,911.01 | Wellesley to Bourne (1-Day, Sat) |
