| 2025 | $225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,476.59 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,145.00 | Reimagined |
| 2020 | $2,725.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,514.56 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,400.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,969.00 | Wellesley to Provincetown Inn (2-Day) |
