| Brenda Kellogg | $1,500.00 |
| 2025 | $1,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $10,255.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $9,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,000.09 | Reimagined |
