| Jaime Curley | $50.00 |
| 2025 | $50.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,364.10 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $4,696.87 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $2,080.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $1,505.00 | Reimagined Teen |
| 2020 | $620.00 | PMC Rider |
