| Doris Brophy | $100.00 |
| 2025 | $100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,220.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $14,895.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $11,590.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $490.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,266.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,975.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $6,625.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,553.38 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $8,103.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,194.09 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $10,064.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $8,228.57 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $10,436.00 | Sturbridge to Provincetown Monument (2-Day) |
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