| 2023 | $6,830.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,659.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $25.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,675.00 | Sturbridge to Provincetown Inn (2-Day) |
