| 2024 | $6,001.68 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,047.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,091.66 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $1,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.32 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,340.00 | Sturbridge to Provincetown Inn (2-Day) |
