| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,594.41 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $8,862.77 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,165.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $11,477.00 | Sturbridge to Provincetown Monument (2-Day) |
