| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $7,040.00 | Wellesley to Provincetown Inn (2-Day) |
| 2020 | $905.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
