While less well known than the Alaska Highway, the construction of the railway to Whittier was one of the great engineering feats of World War II. Two tunnels, 1 mile and 2.5 miles long, were carved through the Chugach Mountains to link the military bases in Anchorage and Fairbanks to a secret saltwater port.

Seward, the main ice-free port in Southcentral Alaska at that time, was considered too vulnerable to Japanese attack, so in 1941–1943 the Army blasted through the mountains and laid the tracks that would ensure the flow of supplies for the defense of Alaska. After the defeat of Japan, the military pulled out of Whittier, but a year later they were back as the Cold War began with the Soviet Union.

Whittier became a permanent base, and large concrete buildings were built at that time. The 14-story Begich Tower (completed in 1954), an unlikely skyscraper in this small village, is near another anomaly, the “City under One Roof,” which once housed 1,000 personnel and was the largest building in Alaska. Why did they build high-rises? To lessen the need for snow removal in a place where the snow sometimes tops 14 feet.

The base was deactivated in 1960, and the buildings were heavily damaged in the 1964 earthquake. One of them is still vacant, but Begich Tower has been restored and converted into condos. A third high-rise, Whittier Manor, was privately built in the 1950s and later turned into more condos. The military presence today is limited to an oil pipeline that supplies military installations in Anchorage. Ships from Princess Cruises and Carnival Cruise Line stop in Whittier, but most of their passengers quickly depart the town.

For nearly half a century the town of Whittier was connected to the road system only via the Alaska Railroad. This changed in 2000, when an $80 million project made it possible for cars to drive in directly from the Seward Highway through two tunnels, one of which is shared with the railroad.