| 2025 | $0.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2024 | $6,276.75 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $9,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $4,230.00 | Sturbridge to Bourne (1-Day, Sat) |
