| 2025 | $0.00 | PMC |
| 2024 | $10,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,090.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $13,372.00 | Reimagined |
| 2021 | $8,785.95 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,400.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,580.91 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,352.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,045.77 | Wellesley to Provincetown Monument (2-Day) |
