| 2025 | $0.00 | PMC Unpaved |
| 2024 | $5,690.00 | PMC Unpaved |
| 2023 | $6,040.00 | PMC Unpaved |
| 2022 | $2,632.55 | Reimagined |
| 2021 | $4,515.00 | Reimagined |
| 2020 | $4,231.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,045.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,690.00 | Wellesley to Provincetown Inn (2-Day) |
