| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $7,023.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,730.00 | Reimagined |
| 2020 | $4,042.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,895.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,198.51 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,317.75 | Sturbridge to Provincetown Inn (2-Day) |
