It could happen if the head of Russian Railways has his way.
According to a March 23 report in The Siberian Times, Russian Railways president Vladimir Yakunin has proposed a plan for a massive trans-Siberian highway that would link his country's eastern border with the U.S. state of Alaska, crossing a narrow stretch of the Bering Sea that separates Asia and North America.
The road would run across the entirety of Russia, linking with existing road systems in Western Europe and Asia.Yakunin said the road would connect Russia with North America via Russia's far eastern Chukotka region, across the Bering Strait and into Alaska's Seward Peninsula.
Assuming a road to Nome were ever built (the idea has been studied by the state of Alaska), a fantasy road trip from London to New York might cover a grueling but presumably photo-op-laden 20,777 kilometers (12,910 miles).
Who the **** would want to put that many miles on a vehicle? This would only be useful if the connecting areas were highly populated/desirable but unfortunately Alaska and eastern Russia are neither
I kinda forgot that travelling in the opposite direction could be a thing.