| 2025 | $1,050.00 | Reimagined |
| 2024 | $21,231.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $21,221.00 | Reimagined |
| 2022 | $20,117.44 | Reimagined |
| 2021 | $18,046.00 | Reimagined |
| 2020 | $17,245.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $13,294.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $11,510.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $9,605.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $8,720.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $8,320.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,553.38 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,501.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $4,268.75 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $6,020.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $5,960.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $5,925.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,651.67 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $4,815.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,590.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $3,620.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $2,426.00 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $2,601.61 | Sturbridge to Provincetown Inn (2-Day) |
