| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $10,531.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,192.20 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,075.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Reimagined |
| 2020 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,136.58 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.18 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,650.18 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
