| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,700.62 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $14,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $13,371.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,810.91 | Sturbridge to Provincetown Monument (2-Day) |
