| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,311.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $7,615.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $7,605.00 | Wellesley to Provincetown Monument (2-Day) |
