In 1908, the Great Race, also known as the Greatest Auto Race, was cosponsored by the French newspaper Le Matin and the New York Times. Following the first major international auto race, the Peking to Paris race won by an Itala in 1907, the two newspapers set out to create an even tougher challenge. Six teams totaling 17 men, driving three cars from France and one each from Germany, Italy and the United States, started out from Times Square on Feb. 12.

The race began in February because the original plan was for the cars to drive the entire distance – from North America to Asia by crossing the ice of the Bering Strait between Alaska and Russia. The winter weather was overwhelming, forcing one of the French cars, a Sizaire-Naudin, to break down after only 44 miles (71 kilometers) in Peekskill, N.Y. A second French car, a Moto Bloc, made it 1,200 miles (1,931 kilometers) before dropping out in Carroll, Iowa, and the third French car, a De Dion-Bouton, was withdrawn by its manufacturer while crossing Japan.

The American hopeful, the Thomas Flyer, was first to arrive in San Francisco. From there, according to the race organizers' plan, it was to catch a ship to Anchorage for an incredible winter drive across Alaska – and then, even more incredibly, across the frozen Bering Strait and on to Vladivostok, Russia. Not surprisingly, it didn't happen. Ten-foot snowdrifts in Alaska forced the organizers to re-route the Thomas back to Seattle and then by ship to Japan, crossing the island before being shipped to Vladivostok.
The German entry, a Protos, was first to arrive in Paris, on July 26, 1908, but the Thomas Flyer, which arrived four days later, was declared the winner. The Protos team was penalized 15 days for taking a train from Ogden, Utah, to Seattle, and the Thomas was awarded an additional 15 days for attempting to follow the original route to Alaska. From

YouTube about The Great Race - (trailer from the soon to be released documentary on the Great Race of 1908 - they are rebuilding 4 of the cars, creating re-enactments, have collected 1,000 photos from the original race)

Click on View Full Article for these next 3:

They are celebrating the 100th anniversary of this race with another race in 2008. They leave NYC on May 30.
Apparently they took a ship across in 1908.

A map of the route in 1908,8.599892&spn=143.314416,281.953125&z=2

Also that page has links to some of the coments in the journal of the winner.

This page has more details from the journals, and many photos.