| 2025 | $250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $12,792.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,751.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $17,365.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $14,621.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,930.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $12,152.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $10,135.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $8,893.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $7,539.50 | Wellesley to Provincetown Monument (2-Day) |
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