| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,016.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $12,237.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,714.87 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,232.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,184.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,036.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,115.50 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,033.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $8,699.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $9,400.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $7,120.00 | Wellesley to Provincetown Monument (2-Day) |
