| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $23,518.04 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $22,390.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $26,181.46 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $19,846.45 | Reimagined |
| 2020 | $19,596.30 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $23,310.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $25,850.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $20,152.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $17,590.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $15,292.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $13,071.12 | Sturbridge to Provincetown Monument (2-Day) |
