| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,659.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $4,215.90 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,392.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,715.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,616.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,617.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,389.24 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,375.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,325.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | 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) |
| 2006 | $3,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,402.00 | Sturbridge to Provincetown Inn (2-Day) |
