| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $9,260.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,740.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,506.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,291.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,810.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $16,807.86 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $13,121.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $6,025.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $16,705.00 | Wellesley to Provincetown Monument (2-Day) |
