| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $18,845.24 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $14,051.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $18,871.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $21,678.44 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $11,269.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,025.85 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,944.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $11,542.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $9,421.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $9,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $9,279.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,456.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,241.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $9,046.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $10,282.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $11,257.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $6,933.34 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $14,053.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $13,207.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $11,127.34 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $9,126.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $8,222.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $9,062.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $9,245.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $8,063.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $38,659.44 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $23,766.75 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $27,399.44 | PMC Rider and Volunteer |
| 1996 | $14,051.00 | PMC Rider |
