| Gini Gerrity |
| 2025 | $100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,496.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $1,550.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,205.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,015.00 | Wellesley to Provincetown Inn (2-Day) |
