| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $10,010.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,595.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $9,742.75 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $4,485.00 | Reimagined |
| 2020 | $4,730.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $8,515.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,598.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $6,880.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,210.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,457.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
