| 2024 | $9,780.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $10,000.47 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,160.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,121.59 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $26,114.14 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,598.02 | Sturbridge to Provincetown Inn (2-Day) |
