| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,040.40 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $4,714.24 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
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