| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $11,390.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,410.00 | Reimagined |
| 2021 | $11,120.00 | Reimagined |
| 2020 | $1,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,745.70 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Sturbridge to Provincetown Inn (2-Day) |
