| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,500.46 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,325.49 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,179.03 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $515.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $24,766.88 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $11,831.00 | Wellesley to Provincetown Monument (2-Day) |
