| 2025 | $0.00 | Reimagined |
| 2024 | $2,000.00 | Reimagined |
| 2023 | $2,084.59 | Reimagined |
| 2022 | $2,021.43 | Reimagined |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $140.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,095.20 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,760.00 | Wellesley to Provincetown Inn (2-Day) |
