| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $110.00 | Virtual Ride |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $4,000.00 | Reimagined |
| 2020 | $1,195.00 | Wellesley to Provincetown Inn (2-Day) |
