| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,675.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,410.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,385.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $7,826.11 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $6,811.11 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.11 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $13,087.25 | Wellesley to Provincetown Inn (2-Day) |
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