| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,283.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $2,000.00 | Reimagined |
| 2021 | $2,001.45 | Reimagined |
| 2020 | $1,160.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
