| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $27,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $19,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $35,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $90.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
