| Mark Dirks | $3,000.00 |
| 2025 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,980.00 | Reimagined |
| 2022 | $10,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $0.00 | PMC Rider |
| 2016 | $100.00 | PMC Rider |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,940.00 | Sturbridge to Provincetown Inn (2-Day) |
