Huerfano County was a crossroads in the American West long before the Europeans arrived. Taos Pueblo, in northern New Mexico, has been a major Native American trading center for over 1,000 years. Trading routes spread out from Taos in all directions but one of the most used trails headed north from Taos into the San Luis Valley and crossed east over the Sangre de Cristo's at Sangre de Cristo Pass, through the gap between Rough Mountain and Sheep Mountain. From there it went down Oak Creek to the Huerfano River, around to the eastern edge of the Wet Mountains and then north along the Wets and the Front Range to the South Platte River. There the trail forked, one branch heading north into Wyoming and Montana, the other following the South Platte into Nebraska.

In those days, the Utes, Navajos, Jicarilla Apaches, and Comanches came and went through Huerfano County. The Spanish Peaks were sacred mountains to these people and they performed lots of ceremonies here. As far as they were concerned, this is where Mankind first emerged from the womb of the Earth into their version of the Garden of Eden (only, they weren't thrown out of Paradise until the Europeans arrived).

The first Europeans to come to Huerfano County were most likely Spanish but there were also a lot of French trappers traveling through. Near where Oak Creek separates from the Huerfano River a settlement called Badito (probably taken from the nearby landmark "Badito Cone") was founded. The Zebulon Pike Expedition in 1806-07 is recognized as the first Americans to officially enter Huerfano County but by that time over 1400 Europeans are recorded to have passed through Badito as they journeyed along the Taos (or Trapper's) Trail. Pike's expedition notified the Spaniards in Santa Fe that the Americans were coming and they responded by sending troops north to build a fort along the southeastern edge of the Wet Mountains, not too far east of Badito, in 1819-20. Then in 1820 came the Mexican Revolution: the Spanish were tossed out and the fort was abandoned. That year also saw William Becknell make the first recorded traverse of the Santa Fe Trail from Missouri to Santa Fe and back. While Becknell didn't come near Huerfano County, he did establish a trail that brought thousands of folks west, and quite a few split off from the Mountain Branch of the Santa Fe Trail and headed west, past Huerfano Butte and up the Huerfano, over Sangre de Cristo Pass and into the San Luis Valley. For years, this was the preferred route for traders heading to Taos who wanted to avoid the customs officials in Santa Fe.

In the beginning of the Colorado Territory days, Huerfano County was much larger, stretching from the Arkansas River south to New Mexico and from the Kansas border to the mountains, but over time it was cut up and portions of the original county became entire new counties. In the earliest days of American "ownership," Badito was still the main center of business and was the official county seat for a couple of years, before Walsenburg became more established and the county offices were moved there (as the fortunes of the fur trade declined, so did Badito). These days, Walsenburg is a hub with roads heading cross-country in all directions. Because of the intersection of the I-25 with US 160 and State Highways 10 and 69, over 4 million vehicles per year make the drive down Main Street.