| 2025 | $1,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,025.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,500.45 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,000.75 | Reimagined |
| 2020 | $9,000.75 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,575.00 | Wellesley to Provincetown Inn (2-Day) |
