| Thomas Bogan | $1,000.00 |
| Thomas Bogan | $10,000.00 |
| 2025 | $11,000.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2024 | $10,250.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2023 | $10,050.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2022 | $10,000.00 | Reimagined |
| 2021 | $10,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $10,090.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $13,160.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $10,775.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $11,350.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $9,059.50 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $7,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $8,325.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $6,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $7,635.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
