| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $8,030.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,061.96 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,129.90 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,170.00 | Reimagined |
| 2020 | $240.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
