| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,171.24 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $8,361.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,925.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,506.23 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,560.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,548.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,805.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,557.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $17,421.15 | Wellesley to Bourne (1-Day, Sat) |
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