| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Wellesley Century |
| 2020 | $1,128.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Inn (2-Day) |
