| 2025 | $0.00 | Reimagined |
| 2024 | $12,806.00 | Reimagined |
| 2023 | $11,891.00 | Reimagined |
| 2022 | $15,221.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $18,541.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $17,950.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $11,870.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,226.63 | Wellesley to Provincetown Inn (2-Day) |
