| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,485.50 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $6,922.65 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,378.25 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $1,371.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,125.56 | Wellesley to Provincetown Inn (2-Day) |
