| 2025 | $170.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,120.54 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $2,440.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2021 | $500.00 | Virtual Ride |
| 2020 | $1,315.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2019 | $2,330.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2017 | $0.00 | PMC Volunteer |
| 2016 | $0.00 | PMC Volunteer |
| 2015 | $0.00 | PMC Volunteer |
| 2014 | $0.00 | PMC Volunteer |
| 2013 | $0.00 | PMC Volunteer |
| 2012 | $0.00 | PMC Volunteer |
| 2011 | $0.00 | PMC Volunteer |
| 2010 | $0.00 | PMC Volunteer |
| 2006 | $0.00 | PMC Volunteer |
| 2005 | $0.00 | PMC Volunteer |
| 2004 | $0.00 | PMC Volunteer |
