| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,570.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $18,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,631.28 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $13,410.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,935.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,240.57 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,170.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,255.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,501.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,902.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,383.07 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,256.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,566.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $5,857.83 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $6,622.66 | Sturbridge to Provincetown Monument (2-Day) |
