| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,099.67 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2023 | $12,816.52 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,278.58 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,852.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,470.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,170.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,820.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,218.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,685.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,494.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,141.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $8,161.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,105.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,621.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $6,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $5,070.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,707.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,580.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,630.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $1,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1987 | $0.00 | PMC Rider |
| 1986 | $0.00 | PMC Rider |
| 1985 | $0.00 | PMC Rider |
| 1984 | $0.00 | PMC Rider |
