| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $6,295.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,356.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,565.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $75.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2017 | $4,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
