| 2025 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,235.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,110.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,110.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $9,400.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $5,085.00 | Wellesley to Bourne (1-Day, Sat) |
