| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,838.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,150.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $12,864.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,717.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,469.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $9,143.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $6,997.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $8,563.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $6,886.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $4,782.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $3,783.25 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $5,461.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $5,450.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,200.18 | Wellesley to Provincetown Monument (2-Day) |
| 2010 | $6,704.00 | Wellesley to Provincetown Monument (2-Day) |
| 2009 | $6,853.18 | Wellesley to Provincetown Monument (2-Day) |
| 2008 | $7,440.00 | Wellesley to Provincetown Monument (2-Day) |
