| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,145.65 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,005.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,615.00 | Reimagined |
| 2020 | $2,116.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,000.01 | Sturbridge to Provincetown Inn (2-Day) |
