| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,755.81 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,338.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,741.00 | Wellesley Century |
| 2020 | $4,730.00 | Sturbridge to Provincetown Monument (2-Day) |
