| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $10,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $11,600.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,595.00 | Reimagined |
| 2020 | $9,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $9,950.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $10,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $8,821.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $6,910.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,550.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $4,095.00 | Sturbridge to Provincetown Monument (2-Day) |
