| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,405.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,778.61 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,165.00 | Wellesley Century |
| 2020 | $1,870.00 | PMC Rider |
