| 2025 | $0.00 | Sturbridge to Bourne + Wellesley to Wellesley |
| 2024 | $3,200.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $6,186.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $3,186.00 | Reimagined |
| 2021 | $9,000.00 | Reimagined |
| 2020 | $3,250.00 | Wellesley to Bourne (1-Day, Sat) |
