| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,075.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $6,751.00 | Reimagined |
| 2020 | $150.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,167.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,655.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,649.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,981.63 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $5,995.00 | Sturbridge to Provincetown Monument (2-Day) |
