| 2025 | $0.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2024 | $5,840.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2023 | $6,500.35 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,867.31 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $5,479.74 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $4,018.99 | Sturbridge to Bourne (1-Day, Sat) |
| 2019 | $5,075.94 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,135.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,320.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,760.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,486.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,715.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $0.00 | PMC Volunteer |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $6,645.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,510.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $3,175.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $2,665.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,325.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,730.00 | Wellesley to Provincetown Inn (2-Day) |
