| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,275.53 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $9,577.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $7,252.55 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $8,088.00 | Wellesley to Provincetown Monument (2-Day) |
