Hispanic folklore has Our Lady of Guadalupe, the patroness of Mexico, guiding colonists to the banks of the Conejos (Spanish, rabbits) River, which runs fast as a jackrabbit down from the San Juan Mountains into the Rio Grande. When Hispanic settlers first rested on the cottonwood-shaded bank of the Conejos in 1854, one of their oxen refused to go any farther. The owner cajoled and cursed, pushed and pulled, but the beast would not budge. Finally someone pointed out that the statue of Our Lady of Guadalupe, which the creature was carrying, had fallen off on that spot. After this sign from heaven, the colonists settled there on the north side of the Conejos River. That summer they built Guadalupe, said to be the oldest town in Conejos County, dug the Conejos Ditch, and built a small chapel for Our Lady of Guadalupe.
This was the first permanent settlement on the Conejos Land Grant, awarded by the governor of New Mexico in 1833 to Seledon Valdez and other residents of Taos County, New Mexico. The Conejos grant covered some 1,600 square miles between the Rio Grande on the east and the San Juan Mountains on the west, from the La Garita Mountains on the north to the round-topped Mount San Antonio just south of the Colorado–New Mexico boundary. The grant was ultimately disallowed in a Santa Fe courtroom in 1895 despite the testimony of Crecencio Valdez, the son of Seledon, that his father had given the Conejos grant deed to Lafayette Head and Alexander C. Hunt to be recorded. That was the last seen of the document. Head spearheaded development of Conejos County and became the first lieutenant governor of Colorado. Hunt, who would become a territorial governor, promoted the Denver & Rio Grande Railroad and its development of the San Luis Valley.
Among U.S. citizens who moved into the valley were Mormons, who planted farming communities at La Jara, Manassa, Romeo (formerly Romero), and Sanford. The D&RG arrived in 1880 and created the new railroad town of Antonito. Thanks to the D&RG connections to stockyards in Denver and elsewhere, Conejos County became the sheep-raising center of Colorado. Between 1900 and 1950 the county grew steadily, peaking at around 12,000. Since then, falling farm and live-stock prices have caused a decline in population to a 1990 count of 7,453. Adobe ruins and graveyards mark the sites of many abandoned communities. Of thirty-seven post office towns once active in the county, most are fading or gone. The county perked up in 1971 with the reconstruction of the D&RG route to Chama, New Mexico, as the Cumbres & Toltec Scenic Railroad, America's longest and highest steam-powered narrow-gauge line.
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