The Yakama people and Interior Salish people traveled this corridor through the Cascades for centuries, connecting the grasslands of the upper Yakima Valley to the damp lowlands of what is now Pierce County. The first written account of the route came in 1841, when Lieutenant Robert E. Johnson of the United States Navy crossed the pass as part of the Wilkes Expedition, a sprawling naval survey of the Pacific. Johnson's report described a rugged but navigable mountain crossing, and word of the route filtered east through the networks of westward migration. By the early 1850s, emigrants heading for the Oregon Territory were looking for alternatives to the long Columbia River route, and Naches Pass offered a more direct line to the growing settlements around Puget Sound.

James Longmire led his family out of Indiana on March 6, 1853, bound for the Pacific Northwest. By late September, his party of more than thirty wagons had reached the upper Yakima Valley, where the Yakama under Chief Owhi offered hospitality in the Wenas Valley. The emigrants followed the Naches River for four days, crossing it fifty-two times as the canyon narrowed and the mountains closed in. At the summit, they found what an 1853 survey had already declared impassable for wagons: a precipitous, nearly vertical cliff face with no road and no alternative route. The settlers improvised. They tied ropes to the wagon axles, looped the other end around a tree trunk, and lowered each wagon one at a time while men braced the line. Every wagon made it down except the Lanes', whose family finished the journey on horseback. After more hard traveling along the Greenwater and White rivers, the party reached Fort Steilacoom on October 9, 1853.

Despite the Longmire crossing, Naches Pass never became a proper road. The dense old-growth forest blanketing the western slopes made construction prohibitively expensive, and when the territorial legislature evaluated the route in 1853, engineers judged it infeasible. Snoqualmie Pass, farther north, won out as the preferred crossing, eventually carrying U.S. Route 10 and then Interstate 90. Naches Pass was proposed as Washington State Route 168 as early as the 1930s, but the designation has never been acted upon. The trail remained unpaved, and as of 2017 it consists of United States Forest Service roads popular with off-road enthusiasts who navigate the same rocky terrain that nearly broke those emigrant wagons more than a century and a half ago.

James Longmire settled on Yelm Prairie after the crossing, but the mountain that had nearly stopped his wagons kept pulling him back. In 1883, at the age of sixty-three, he reached the summit of Mount Rainier. That same year he discovered the mineral hot springs on the mountain's southern flank that still bear his name. The Longmire family developed the springs into a tourist destination, and the settlement of Longmire became the first developed area in what would become Mount Rainier National Park. The trail itself endures as a ghost of the emigrant era, its ruts still visible in places beneath the second-growth timber. From the air, Naches Pass is a low saddle in the Cascade ridgeline north of Rainier, a gap that looks deceptively gentle from cruising altitude but hides the vertical drama that tested every family who ever rolled a wagon to its edge.