| 2025 | $3,648.30 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,048.88 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $9,673.12 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,078.00 | Reimagined |
| 2021 | $3,907.00 | Reimagined |
| 2020 | $6,188.40 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $4,347.99 | Sturbridge to Provincetown Monument (2-Day) |
| 2002 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
