| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,962.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,032.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $2,503.20 | Reimagined |
| 2021 | $3,355.00 | Wellesley Century |
| 2020 | $1,375.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
