| 2025 | $585.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Reimagined |
| 2022 | $6,085.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,050.00 | Reimagined |
| 2020 | $1,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,225.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,161.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,699.79 | Sturbridge to Provincetown Inn (2-Day) |
