| Mary Holtze | $250.00 |
| Elena Langlois | $250.00 |
| 2025 | $500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,079.34 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,015.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $7,115.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,045.00 | Wellesley Century |
| 2020 | $6,444.05 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,115.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,550.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,975.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,521.25 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,506.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $5,165.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,325.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $65.00 | PMC Volunteer |
| 2008 | $4,050.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,740.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,895.00 | Wellesley to Provincetown Monument (2-Day) |
