| 2025 | $0.00 | Reimagined |
| 2024 | $5,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $8,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $10,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $1,324.79 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,387.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $10,988.30 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $5,022.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
