| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,435.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,767.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,998.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $15,269.00 | Reimagined |
| 2020 | $12,275.00 | Sturbridge to Provincetown Monument (2-Day) |
