| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $10,030.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $11,410.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $4,020.00 | Virtual Ride |
| 2021 | $9,641.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,460.00 | Wellesley to Bourne (1-Day, Sat) |
