| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $10,000.00 | Wellesley to Bourne + Wellesley to Patriot Place |
| 2023 | $14,329.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $10,005.38 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $8,070.13 | Reimagined |
| 2020 | $7,546.45 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $10,567.50 | Wellesley to Provincetown Monument (2-Day) |
