| 2024 | $6,205.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,225.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,522.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,440.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $75.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,602.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,591.40 | Sturbridge to Provincetown Inn (2-Day) |
