| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2024 | $21,240.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $23,060.30 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $27,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $24,544.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $18,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $22,310.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $34,055.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $31,370.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $30,055.00 | Sturbridge to Provincetown Monument (2-Day) |
