| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,140.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $8,460.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,918.48 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $4,820.00 | Reimagined |
| 2020 | $4,940.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,601.13 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $11,978.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,152.25 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Wellesley to Provincetown Inn (2-Day) |
