| Maxwell Sloan | $60.00 |
| Peter Bulavinetz | |
| Dave Levin | |
| Luke Taylor |
| 2025 | $480.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,627.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,180.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $4,331.00 | Reimagined |
| 2020 | $700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,101.00 | Sturbridge to Provincetown Inn (2-Day) |
