| 2025 | $500.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $13,488.80 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $15,447.10 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $14,920.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $16,211.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $14,885.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $13,304.50 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $16,425.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $12,102.24 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,837.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $17,125.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $13,105.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $11,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $10,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $9,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $8,875.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $7,925.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $8,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $10,600.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $10,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $10,430.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $10,349.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $10,255.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $7,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $5,100.00 | Sturbridge to Provincetown Inn (2-Day) |
