| Gwendolyn OMalley |
| 2022 | $4,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
