| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,451.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,471.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $10,160.00 | Reimagined |
| 2020 | $9,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,478.16 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,763.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,413.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,175.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,309.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,205.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $6,190.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,516.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,560.00 | Sturbridge to Bourne (1-Day, Sat) |
