Throughout the 1800s, the United States, Washington Territory, and private parties explored the construction of a wagon road or railroad over the pass, but nearly all such attempts failed.
Accompanied by Cornelius Rogers, an associate of Dr. Marcus Whitman at Waillatpu mission, Pambrun crossed Naches pass.
[3][4]: 64 Emigrants arriving in Portland, Oregon Territory, who wished to continue north had to slog up the muddy Cowlitz Trail, first by river and then overland, to the southern end of Puget Sound.
Unwilling to wait for the slow-moving federal government to act, and in order to attract 1853 emigrants already en route, the citizens of Puget Sound collected funds to send Edward Jay Allen, John Edgar, George Shazer and Whitfield Kirtley into the field to survey the Naches Pass route to determine its suitability as a wagon road.
[4]: 62–81 Meanwhile, Captain George B. McClellan received specific orders in April, 1853 from both Governor Isaac Stevens and Secretary of War Jefferson Davis to search the Cascade passes for an appropriate route for a military wagon road, to build the road in time for use by that fall's emigrant migration, and to determine the suitability of the various passes as a route for a future railroad.
One team, led by Edward Jay Allen, worked east from the Puyallup valley to Naches Pass and a few miles beyond.
On September 12 Andrew Moore, a member of Olympia's road committee, tracked the captain down near present-day Ellensburg and got him to agree to put Allen's men under government contract.
Apparently satisfied that he had fulfilled his orders in regards to building a road over the mountains, McClellan continued his journey north, anticipating his upcoming rendezvous with Governor Stevens who was working his way west from Minnesota.
The emigrants broke out of the forest and into open prairie country at the site of present-day Enumclaw and arrived at Fort Steilacoom in mid-October.
In the 1920s, Ezra Meeker lobbied mightily to get the state legislature to select the Naches Pass route for a southern cross-state highway.
The deep dollars of the railroads and their plans to build a hotel on the north side of Mount Rainier National Park led to the creation of the Chinook Pass highway instead.