| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $14,727.98 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,301.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,026.58 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $12,150.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $4,937.30 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $11,392.10 | Sturbridge to Wellesley (2-Day) |
| 2018 | $8,472.10 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,675.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $6,901.23 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $5,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $4,830.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,755.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $6,100.00 | Sturbridge to Wellesley (2-Day) |
| 2008 | $7,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $8,585.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $5,435.00 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| 2005 | $5,185.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $6,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,995.00 | Sturbridge to Provincetown Inn (2-Day) |
