| 2023 | $6,044.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $10,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $265.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
