| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,479.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,107.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,573.00 | Wellesley Century |
| 2020 | $7,359.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,691.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Monument (2-Day) |
