| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,940.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $7,320.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $5,205.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $1,315.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,002.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
