| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $18,120.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $13,740.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $10,040.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $10,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $290.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $20,005.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $10,101.13 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $5,450.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $5,240.00 | Wellesley to Provincetown Monument (2-Day) |
