| 2025 | $0.00 | PMC |
| $3,429.65 | PMC Unpaved | |
| 2024 | $1,500.00 | PMC Unpaved |
| 2023 | $1,500.00 | PMC Unpaved |
| 2021 | $25.00 | PMC Fundraiser |
| 2019 | $50.00 | PMC Rider |
| 2018 | $4,925.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $25.00 | PMC Rider |
| 2015 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,605.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Monument (2-Day) |
