| 2025 | $0.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $401,300.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $401,400.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $401,300.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2021 | $50,550.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $50,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $25,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $25,269.67 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $32,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $30,260.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $22,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $18,920.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $21,303.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $15,069.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $14,217.50 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $13,465.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $13,976.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $17,114.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $19,405.25 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $9,942.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $7,599.81 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $10,860.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $6,661.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $6,662.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $7,619.15 | Sturbridge to Provincetown Inn (2-Day) |
