| 2024 | $6,248.86 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,500.22 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,153.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,098.61 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $5,000.22 | Sturbridge to Provincetown Inn (2-Day) |
