| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $8,630.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,925.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $9,915.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,750.00 | Wellesley to Wellesley (50 mile Sunday) |
