| 2025 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $15,238.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $11,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $13,750.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $12,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,211.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,570.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
