| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $1,250.00 | Virtual Ride |
| 2023 | $10,244.46 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,500.26 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,002.31 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,595.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,461.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,292.00 | Sturbridge to Provincetown Inn (2-Day) |
