| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,125.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,680.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $60.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,624.28 | Wellesley to Provincetown Monument (2-Day) |
