| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2004 | $3,050.00 | Wellesley to Provincetown Monument (2-Day) |
| 2003 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,030.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,415.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,007.00 | Wellesley to Provincetown Inn (2-Day) |
