| Olivia Gobin | $30.00 |
| 2025 | $1,255.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,000.55 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,340.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,455.75 | Reimagined |
| 2020 | $9,120.25 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,350.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.13 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $11,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,964.84 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $11,175.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $9,700.00 | Wellesley to Bourne (1-Day, Sat) |
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