| 2025 | $500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $4,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2005 | $3,040.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $1,758.92 | Sturbridge to Bourne (1-Day, Sat) |
