| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $4,200.00 | Wellesley Century |
| 2020 | $5,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $6,600.00 | Wellesley to Provincetown Inn (2-Day) |
