| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $90.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $16,475.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,825.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
