| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $7,190.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,450.00 | Sturbridge to Provincetown Inn (2-Day) |
