| Carmine and Lisa Timmoneri | $500.00 |
| Karolina Kowalska | $800.00 |
| Royal Green Appliance | $500.00 |
| David Berger | $150.00 |
| 2025 | $1,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,030.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,638.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
