| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $7,451.96 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,050.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,215.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $5,405.00 | Wellesley Century |
| 2020 | $5,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,520.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,645.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $8,075.78 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,655.00 | Sturbridge to Provincetown Monument (2-Day) |
