| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Reimagined |
| 2021 | $6,275.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $2,770.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
