| 2025 | $0.00 | PMC |
| 2024 | $7,506.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,530.00 | Reimagined |
| 2021 | $2,685.00 | Reimagined |
| 2020 | $2,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,620.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
