| 2024 | $15,391.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2020 | $1,500.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2019 | $4,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Monument (2-Day) |
