| 2019 | $745.00 | PMC Fundraiser |
| 2018 | $23,647.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $3,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2008 | $4,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $1,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,100.00 | Sturbridge to Provincetown Inn (2-Day) |
