| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $2,000.00 | Reimagined |
| 2022 | $5,500.11 | Reimagined |
| 2021 | $2,685.50 | Reimagined |
| 2020 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,120.00 | Wellesley to Provincetown Inn (2-Day) |
