| Scott Stevens |
| 2025 | $30.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $19,986.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $23,751.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $22,401.90 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $20,861.11 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $14,431.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $14,990.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $21,138.52 | Sturbridge to Provincetown Monument (2-Day) |
