| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,305.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,874.20 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,800.65 | Wellesley to Provincetown Inn (2-Day) |
| 2020 | $90.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $4,010.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,101.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,835.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,461.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,305.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,326.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,211.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,235.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $4,230.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,610.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $3,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $0.00 | PMC Volunteer |
| 2004 | $0.00 | PMC Volunteer |
