| 2025 | $0.00 | Reimagined |
| 2024 | $6,006.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,600.00 | Reimagined |
| 2021 | $3,944.20 | Wellesley Century |
| 2020 | $125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,167.42 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,525.00 | Sturbridge to Provincetown Inn (2-Day) |
