| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,033.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,720.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,570.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $7,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,290.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $5,700.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $4,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
