| 2025 | $0.00 | Reimagined |
| 2024 | $19,771.94 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $31,318.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $25,342.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $20,300.50 | Reimagined |
| 2020 | $15,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $18,160.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $17,145.00 | Sturbridge to Provincetown Inn (2-Day) |
