| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,154.89 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,400.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $40.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
