| Kevin McLarnon | $1,000.00 |
| 2025 | $1,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $13,813.33 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,522.38 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $8,256.00 | Reimagined |
| 2020 | $3,397.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,369.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,670.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $5,801.63 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $5,442.56 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,921.89 | Sturbridge to Provincetown Inn (2-Day) |
