| 2025 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $13,510.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $18,865.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $13,572.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $8,785.95 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,630.91 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,008.00 | Sturbridge to Provincetown Monument (2-Day) |
