| 2025 | $0.00 | Sturbridge to Bourne (1-Day, Sat) and Volunteer |
| $0.00 | PMC Unpaved | |
| 2024 | $11,159.20 | Sturbridge to Bourne (1-Day, Sat) and Volunteer |
| 2023 | $12,477.10 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| 2022 | $12,867.10 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| 2021 | $12,762.10 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $9,012.48 | Sturbridge to Bourne (1-Day, Sat) and Volunteer |
| 2019 | $6,000.00 | PMC Virtual Rider and Volunteer |
| 2018 | $9,888.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $9,425.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $9,600.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $9,080.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,264.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,785.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,706.94 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $4,240.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2009 | $5,572.00 | Sturbridge to Provincetown Monument (2-Day) |
