| Jasmine Adams | $50.00 |
| 2025 | $150.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $7,286.37 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,070.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,020.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,988.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,580.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,116.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,859.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,701.69 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,609.89 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $5,171.09 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,408.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,220.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,668.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $4,185.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $3,614.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,105.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,779.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $1,500.00 | Sturbridge to Bourne (1-Day, Sat) |
