| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $12,506.58 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $9,071.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,730.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $7,825.00 | Reimagined |
| 2020 | $8,006.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,520.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,375.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,642.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $5,633.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $7,738.90 | Sturbridge to Provincetown Monument (2-Day) |
