| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,289.25 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,105.02 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,868.32 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,496.50 | Reimagined |
| 2020 | $6,295.00 | Sturbridge to Bourne (1-Day, Sat) |
