| 2025 | $0.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $20,000.00 | Virtual Ride |
| 2023 | $30,000.00 | Reimagined |
| 2022 | $20,000.00 | Reimagined |
| 2021 | $22,000.00 | Reimagined |
| 2020 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $21,542.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $18,892.94 | Sturbridge to Provincetown Inn (2-Day) |
