| 2020 | $120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,015.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,123.12 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.34 | 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 | $6,925.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,455.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
