| 2025 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $35,320.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $45,445.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $46,875.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $45,265.24 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $19,665.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $25,125.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $19,450.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $22,188.33 | Wellesley to Bourne (1-Day, Sat) |
