| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,081.57 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2021 | $5,186.00 | Wellesley Century and Volunteer |
| 2020 | $1,834.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,186.24 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,356.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $5,064.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,472.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,454.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $8,540.27 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,351.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,473.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,816.97 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,228.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $8,841.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $7,513.00 | Wellesley to Provincetown Monument (2-Day) |
