| Jamison Hagerman | |
| Louise and Jason Langheier | $22.00 |
| 2025 | $122.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $1,990.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,967.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,304.37 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,738.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,530.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,088.32 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $5,450.00 | Sturbridge to Provincetown Inn (2-Day) |
