| Casey Brock-Wilson | $250.00 |
| Anne Haakansson | $30.00 |
| 2025 | $280.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $12,930.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $14,040.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $8,576.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $11,816.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $165.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $9,128.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $15,798.30 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $12,752.82 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $5,262.12 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $5,110.25 | Wellesley to Provincetown Inn (2-Day) |
