| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,280.03 | Reimagined |
| 2023 | $17,097.10 | Reimagined |
| 2022 | $15,097.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,148.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,560.00 | Sturbridge to Provincetown Inn (2-Day) |
