| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $11,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $10,425.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $16,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $9,620.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $9,297.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $7,850.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Monument (2-Day) |
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