| 2025 | $0.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $3,000.00 | Reimagined |
| 2023 | $10,000.11 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $10,641.00 | Reimagined |
| 2021 | $7,335.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,540.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,501.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,325.00 | Wellesley to Provincetown Inn (2-Day) |
