| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $17,580.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,035.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $90.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,118.60 | Sturbridge to Provincetown Inn (2-Day) |
