| 2024 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,056.10 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
