| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,460.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,072.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $2,616.00 | Wellesley to Provincetown Monument (2-Day) |
