| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,692.95 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,291.06 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,855.58 | Wellesley Century |
| 2020 | $6,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,297.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,795.00 | Sturbridge to Provincetown Monument (2-Day) |
