| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,821.94 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,004.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,264.69 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $8,233.92 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $35.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,778.75 | Sturbridge to Provincetown Inn (2-Day) |
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