| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $18,765.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $11,360.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $12,549.43 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,580.00 | Sturbridge to Bourne + Wellesley Century (2-Day) |
| 2020 | $9,275.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $10,250.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $8,310.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $9,035.00 | Sturbridge to Provincetown Monument (2-Day) |
