| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,941.84 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $6,835.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,053.56 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,050.00 | Wellesley to Bourne (1-Day, Sat) |
| 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) |
