The Chicago, Milwaukee, St. Paul and Pacific Railroad (commonly known as the Milwaukee Road) used the pass for its crossing of the Continental Divide on its mainline between Chicago, Illinois and the Pacific Northwest.

The line was built as part of the Milwaukee Road's Pacific Extension, which was completed in 1909.

A poor competitive position against the rival Burlington Northern Railroad and substantial losses caused the Milwaukee Road to abandon the line in 1980.

Pipestone Pass was also used (without a tunnel) as the Continental Divide crossing for U.S. Highway 10, dating from 1926.

Hosted by Butte's Piss and Moan Running Club, the Wulfman CDT 14k is held on the Saturday closest to the Summer solstice.