| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $14,878.53 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $14,437.16 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $14,343.29 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $14,888.87 | Wellesley Century |
| 2020 | $15,558.41 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $9,852.65 | Sturbridge to Provincetown Inn (2-Day) |
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