| 2025 | $6,225.00 | Reimagined |
| 2024 | $6,000.00 | Reimagined |
| 2023 | $16,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $14,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $5,000.00 | Virtual Ride |
| 2020 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,580.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $13,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $17,320.00 | Sturbridge to Provincetown Monument (2-Day) |
