| 2025 | $0.00 | PMC Virtual Rider |
| $0.00 | PMC Unpaved | |
| 2024 | $2,057.02 | Virtual Ride |
| $4,430.00 | PMC Unpaved | |
| 2023 | $8,338.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,730.00 | PMC Unpaved | |
| 2022 | $11,210.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $5,695.00 | Reimagined |
| 2020 | $5,075.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $7,095.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,300.00 | PMC Rider |
| 2017 | $5,665.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $5,575.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,480.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,726.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,873.00 | Sturbridge to Provincetown Inn (2-Day) |
