| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,121.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,121.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,025.00 | Wellesley Century |
| 2021 | $3,100.00 | Wellesley Century |
| 2020 | $2,075.00 | Sturbridge to Provincetown Monument (2-Day) |
