| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $17,170.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $14,740.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,948.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,090.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,905.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $7,205.00 | Sturbridge 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 | $4,825.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,045.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,560.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $7,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $6,145.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $6,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $10,227.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $6,490.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $4,060.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $4,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,935.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,663.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $2,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,492.50 | Sturbridge to Bourne (1-Day, Sat) |
