| 2025 | $1,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,985.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $12,693.20 | Reimagined |
| 2022 | $9,905.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,232.22 | Reimagined |
| 2020 | $11,296.97 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,419.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,286.61 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,921.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $9,413.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $11,609.85 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,553.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,772.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,275.37 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $25.00 | PMC Virtual Rider |
| 2009 | $6,800.00 | Sturbridge to Wellesley (2-Day) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $50.00 | PMC Volunteer |
