| 2025 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,750.50 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,041.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $10,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2003 | $2,691.35 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,425.00 | Sturbridge to Provincetown Inn (2-Day) |
