| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| $0.00 | PMC Winter Cycle | |
| 2024 | $20,320.50 | Sturbridge to Provincetown Inn (2-Day) |
| $1,550.00 | PMC Unpaved | |
| 2023 | $15,466.50 | Sturbridge to Provincetown Inn (2-Day) |
| $3,100.00 | PMC Unpaved | |
| $500.00 | PMC Winter Cycle | |
| 2022 | $20,324.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,580.00 | PMC Unpaved | |
| 2021 | $20,649.28 | Reimagined |
| 2020 | $19,683.44 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $16,695.67 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $16,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $15,195.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $15,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $15,375.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $14,301.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $13,580.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $14,980.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $12,421.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $10,007.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $10,578.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $14,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $15,531.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $13,990.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $11,839.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $14,115.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $13,935.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $24,920.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $0.00 | PMC Volunteer |
