| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,943.29 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,529.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,595.06 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,327.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $7,847.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,607.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,804.86 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,374.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,044.81 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $8,307.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,399.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,794.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $5,321.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $9,121.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,665.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,121.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,586.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2001 | $3,606.40 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 1999 | $3,262.66 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 1998 | $2,578.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 1997 | $2,646.00 | PMC Rider and Volunteer |
| 1996 | $2,109.00 | PMC Rider and Volunteer |
| 1995 | $1,253.00 | PMC Rider and Volunteer |
| 1994 | $1,800.00 | PMC Rider and Volunteer |
| 1993 | $1,800.00 | PMC Rider and Volunteer |
| 1992 | $2,003.00 | PMC Rider and Volunteer |
| 1991 | $1,695.66 | PMC Rider |
| 1990 | $1,284.00 | PMC Rider |
| 1989 | $1,400.00 | PMC Rider |
| 1988 | $0.00 | PMC Rider |
