| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $5,180.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $1,000.00 | Virtual Ride |
| 2021 | $8,292.52 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $945.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,570.32 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,800.00 | Sturbridge to Provincetown Monument (2-Day) |
