Nobody has ever driven from Russia into Alaska; there is sea in between which rarely freezes and is not stable even when it does. It's also very difficult (physically and bureaucratically) to get anywhere near the easternmost point of Russia, and there is no legal process to cross from Russia to America.
Winter (Dec - Mar) is the best time to travel in the Far East of Russia (though you'll need to modify a diesel vehicle), but from Russia to the USA you would need to ship, most likely through South Korea or Japan.
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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.
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