| Derek Glynn |
| 2025 | $150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $13,618.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $14,805.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,140.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $14,912.10 | Reimagined |
| 2020 | $90.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $12,595.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,730.00 | Sturbridge to Provincetown Inn (2-Day) |
