| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,017.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,399.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,735.05 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $5,150.00 | Reimagined |
| 2020 | $4,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,390.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,745.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,901.45 | Sturbridge to Provincetown Inn (2-Day) |
