| 2025 | $7,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $12,854.99 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $17,065.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $14,911.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $20,072.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $6,481.55 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,872.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $10,268.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $14,409.25 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $10,245.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $5,175.00 | Wellesley to Provincetown Inn (2-Day) |
