Crossing Russia

I have a plan of driving up to Alaska, abandoning my car and then travelling across Russia towards Moscow. Unfortunately I’ve discovered that the Trans Siberian Railroad doesn’t go up to the Bering Strait. What options do I have where I could just cross the Bering Strait and head westward?
The trip would go from there to Moscow then into western Europe or down to the Black Sea and into the Mediterranean.

For one thing, you can’t even drive to the Bering Strait even on the Alaska side. The only roads in that part of Alaska are in the Nome area, but those roads don’t connect with the rest of the continent.

As far as I know your best bet, if you really want to drive to Alaska to start this trip is to drive to Anchorage, catch a flight on Aeroflot to Vladivostok where you can catch the Trans-Siberian across to Moscow. There are no roads that connect to the outside world in Russian East Asia either, just the railroad.

Well, you need to prepare for a long hike or perhaps a horse ride - Siberia is pretty sparsely populated, and there simply aren’t enough roads (or cities close enough together for an off-road vehicle). I remember reading that most travel from larger areas to places in Siberia is done with light aircraft now, since there just aren’t enough roads to drive anywhere, and only a small slice of the land is near the rail line.

Since you’re willing to take a train, you could use a boat - go up to Alaska and sail along the coast until you get to Vladivostock, then take the train. I’m not really sure what your goal is with this trip, but that would seem to be direct travel and not something long distance like airline travel.