| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,260.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,160.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,175.00 | Reimagined |
| 2020 | $60.51 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,081.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,986.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $5,052.00 | Sturbridge to Provincetown Monument (2-Day) |
