| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $22,527.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $20,273.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $18,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $17,245.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $7,095.00 | Sturbridge to Wellesley (2-Day) |
| 2019 | $14,460.00 | Sturbridge to Wellesley (2-Day) |
