| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $107,310.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $111,565.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $123,611.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $136,255.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $102,705.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $75,750.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $50,825.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $37,123.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $17,390.62 | Wellesley to Bourne (1-Day, Sat) |
