| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,979.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,740.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,817.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,880.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,485.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,001.00 | Sturbridge to Provincetown Inn (2-Day) |
