| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $15,951.31 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $12,252.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $12,439.20 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,105.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,620.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,608.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,595.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | 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 | $4,384.38 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $3,375.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $3,725.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $3,100.37 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $3,150.00 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $3,330.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,450.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $2,300.00 | Wellesley to Bourne (1-Day, Sat) |
| 2005 | $3,755.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $1,900.00 | Wellesley to Bourne (1-Day, Sat) |
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