| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $28,121.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $31,619.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $28,257.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $36,337.00 | Reimagined |
| 2020 | $4,875.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $31,241.84 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $50,521.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $29,098.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $20,875.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $12,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $28,515.16 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $33,535.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $25,195.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $16,839.54 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $9,235.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $11,761.00 | Sturbridge to Provincetown Monument (2-Day) |
