| Emily Hodge | $150.00 |
| 2025 | $150.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $12,195.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,880.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $12,155.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,471.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.13 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $9,140.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,511.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,782.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,629.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,397.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,555.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,265.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $6,043.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,171.67 | Wellesley to Provincetown Inn (2-Day) |
