| 2024 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $5,850.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $4,590.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,050.00 | Wellesley to Provincetown Inn (2-Day) |
