| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $42,951.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $35,110.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $38,431.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $23,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $75,126.00 | Sturbridge to Provincetown Inn (2-Day) |
