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If you drive straight through without stopping, it would be roughly 8.5 hours. You're better off taking I-81 through VA than to double back to I-95. I'm a native of the NYC area and have driven to Winston before. If you take I-81 you battle two lanes of 18-wheelers for most of the trip, but if you take I-95 you're stuck dealing with DC, Baltimore, Delware Bridge, and the Jersey Turnpike which are all extremely unpredictable as far as traffic is concerned. When I have driven to Winston in the past, I've always assumed at least 10 hours.
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