| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,018.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,050.00 | Wellesley Century |
| 2020 | $230.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
