| 2025 | $0.00 | Reimagined |
| 2024 | $7,789.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,078.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $4,895.64 | Reimagined |
| 2021 | $4,483.50 | Wellesley Century |
| 2020 | $4,103.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
