| Henry Viarengo | $50.00 |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,664.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $11,441.39 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $1,990.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,251.46 | Sturbridge to Provincetown Monument (2-Day) |
