Uncle Dick’s Toll Road

The Goodnight-Loving Trail wasn’t the longest, oldest, or most heavily traveled of all the old cattle trails, but it was as drenched in legend and lore as any of them. Named for pioneer Panhandle rancher Charles Goodnight and his best friend and partner in commerce, Oliver Loving, the trail extended from Young County to the fable Horsehead Crossing on the Pecos River and north to Colorado. 

Loving blazed the northern extension of the trail in 1866, across the well-watered valleys of northeastern New Mexico, before encountering the narrow and unforgiving Raton Pass, the only route through the otherwise impassable Sangre de Christo Mountains. The alternative was to take the arid plains of Kansas and Oklahoma, where the wide-open spaces provided easy targets for war parties and outlaws. 

What others saw as an obstacle, a former mountain man, scout and explorer named Dick Wootton (usually referred to as Uncle Dick Wootton) saw an opportunity. He secured a charter from the legislatures of New Mexico and Colorado to build a toll road through Raton Pass. 

Using Ute labor, Wootton dramatically altered the geography of the pass to build a 27-mile road that made the pass much easier to navigate. He constructed a road house at the site and people said he carried silver dollars to the bank by the wagonload. When a Colorado commissioner’s court deemed Wootton’s toll too high, he lowered his rates on the Colorado side but jacked up prices on the New Mexico end to make up the difference.

J. Evetts Haley, in his biography of Goodnight, describes Wootton as “sly, crafty and self-sufficient, as wise in the ways of the Rockies as any Ute Indian” and placed him second only to Kit Carson as a scout and frontiersman. 

When Goodnight, his crew and a large herd of longhorns reached Raton Pass, Goodnight and Wootton, two men not known for backing down, had a meeting of the minds. Wootton wanted 10 cents apiece for every cow that used his toll road, a price that Goodnight compared, in his usual profane way, to highway robbery. 

Goodnight fumed that he would find another pass through the mountains, which tickled the old mountain man, who assured him there wasn’t one. Goodnight paid up, but he considered the matter far from settled. He later trailed a course some 50 miles to the east of Loving’s route, which took him through the Sangre De Cristos at Trinchera Pass. Other benefits aside, no one charged a toll on this portion of the trail. 

Wootton was stubborn but he wasn’t stupid. He knew he had erred. He knew that other outfits followed where Goodnight led. He tried to win Goodnight’s favor by letting him take his cattle through Raton Pass free of charge. But Goodnight was not inclined to do Uncle Dick any favors. He drove his cattle through Trinchera Pass and hundreds of other outfits followed. 

Uncle Dick maintained his toll road until 1879, when the Atchison, Topeka and Santa Fe Railroad bought the right of way. People expected the cranky old mountain man to protest or hold out, but he did no such thing. He saw the future and it was a railroad, not a toll road. 

“I just got out of the way of that locomotive,” he said. 

Wootton moved to Trinidad after he closed his toll road and died there in 1893 at the age of 77. Goodnight remained his legendary self until he died in 1929 at age 93. Fifty-six years later, Goodnight, Loving, and their trail provided the inspirations and setting for Larry McMurtry’s masterpiece, Lonesome Dove.