| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $11,295.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $10,467.33 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,536.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $5,159.00 | Wellesley Century |
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