| 2025 | $0.00 | Reimagined |
| 2024 | $8,655.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Reimagined |
| 2022 | $10,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,360.00 | Wellesley Century |
| 2020 | $2,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $18,210.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,990.00 | Sturbridge to Provincetown Inn (2-Day) |
