| 2024 | $6,390.31 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2020 | $3,855.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,927.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,125.00 | Sturbridge to Provincetown Monument (2-Day) |
