| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,372.93 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Reimagined |
| 2021 | $2,680.00 | Reimagined |
| 2020 | $1,845.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,595.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,505.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,125.00 | Sturbridge to Provincetown Inn (2-Day) |
