| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,407.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $9,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,100.00 | Reimagined |
| 2020 | $5,605.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $13,067.09 | Sturbridge to Provincetown Monument (2-Day) |
