| Commonwealth Cares Fund Inc | $250.00 |
| 2025 | $250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $1,550.00 | Virtual Ride |
| 2023 | $10,245.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,897.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,392.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $3,540.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,423.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | PMC Rider |
| 2015 | $9,085.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $14,223.06 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $11,189.00 | Wellesley to Wellesley (2-Day) |
| 2011 | $13,413.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $8,927.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $9,799.80 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $6,975.00 | Wellesley to Provincetown Inn (2-Day) |
