| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $9,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $13,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $15,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $12,540.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $13,430.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $12,525.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $15,675.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $15,750.00 | Wellesley to Provincetown Inn (2-Day) |
