| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $3,665.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $5,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,675.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Monument (2-Day) |
