| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $103,986.50 | Reimagined |
| 2023 | $106,147.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $131,921.64 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $153,102.48 | Wellesley Century |
| 2020 | $16,790.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,880.00 | Sturbridge to Provincetown Inn (2-Day) |
