| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $6,283.42 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,385.00 | Wellesley Century |
| 2020 | $965.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,896.05 | Sturbridge to Provincetown Inn (2-Day) |
