| 2022 | $9,657.10 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $9,237.10 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $1,240.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $11,045.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $8,050.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,626.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,874.44 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
