| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| $0.00 | PMC Unpaved | |
| 2024 | $9,666.55 | Wellesley to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2023 | $7,900.00 | Wellesley to Provincetown Monument (2-Day) |
| $4,000.00 | PMC Unpaved | |
| 2022 | $9,700.00 | Wellesley to Provincetown Monument (2-Day) |
| $2,000.00 | PMC Unpaved | |
| 2021 | $12,925.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $6,975.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,255.40 | PMC Virtual Rider and Volunteer |
| 2018 | $8,027.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $8,655.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $1,560.00 | PMC Rider |
| 2015 | $4,600.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $5,575.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $5,241.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $6,530.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $6,780.00 | Wellesley to Provincetown Monument (2-Day) |
| 2010 | $5,548.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $5,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $4,025.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $4,640.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $3,765.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2004 | $2,750.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $2,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $0.00 | PMC Volunteer |
| 2000 | $1,505.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $1,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 1998 | $1,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 1997 | $1,000.00 | PMC Rider |
