| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,317.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,825.08 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,920.00 | Reimagined |
| 2020 | $4,399.51 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,217.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,175.27 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,845.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,605.22 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,810.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $40.00 | PMC Rider |
| 2011 | $4,042.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,225.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,890.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,735.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,895.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,483.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,611.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,884.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,634.94 | Sturbridge to Bourne (1-Day, Sat) |
| 1999 | $0.00 | PMC |
| 1998 | $1,333.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $0.00 | PMC Volunteer |
