Caleb Greenwood (c. 1783 – c. 1850) was a Western U.S. fur trapper and trail guide. Born in Virginia, Greenwood took part in trapping expeditions organized by associates of John Jacob Astor in 1810 and by Manuel Lisa in 1812-1813. In 1815 he trapped independently on the Arkansas River, and later traveled up the Missouri River in the company of other trappers.
In 1824 trappers led by John Henry Weber, including Greenwood and Jim Bridger, crossed South Pass to trap on the eastern slope of the Wind River Mountains. Weber's party went to what is today Soda Springs, Idaho, and proceeded to a tributary of the Bear River to establish a winter camp. On May 23, 1825, Weber's party joined with a group led by Jedediah Smith in a confrontation with Hudson's Bay Company trappers led by Peter Skene Ogden. In July 1825, Greenwood joined the large group of trappers and traders at William H. Ashley's first great rendezvous on the Green River.
In the 1820s, Greenwood married Batchicka Youngcau, who was half French and half Crow Indian according to family records. The couple had seven children: John (1827 or 1828), Britton Bailey (between 1827 and 1830), Governor Boggs (between 1834 and 1836), William Sublette (1838), James Case (1841), Angeline (dob unknown), and Sarah Mojave (1843). After 1834, he and a growing family lived for a time on a small farm in northern Missouri. After his wife's death in 1843, he again turned to the west. He died in California either in 1849 or 1850. A history of California published by Theodore Henry Hittell in 1898 reports on a conflict between Indians and white settlers, including Greenwood's family, in Coloma, California. This account identifies an additional Greenwood son, David Crockett Greenwood. (Hittell, p. 890)
In 1844 Greenwood, along with Isaac Hitchcock, guided the influential Stephens-Townsend-Murphy Party across the Sierra Nevada mountain range. Reputedly 80 years old at the time, on reaching Sutter's Fort he had completed one of the first overland wagon journeys to California.
Returning east the following year with his two sons, Greenwood pioneered a new route bypassing the Truckee River Canyon. This subsequently became a main route of the California Trail, which hundreds of thousands of people followed in the California Gold Rush of 1849. While guiding the Stephens-Townsend-Murphy party along the Emigrant Trail in Wyoming, Greenwood suggested instead of following the original trail south to Fort Bridger, the party leave the main trail near the Little Sandy River and head west across the Wyoming high desert to rejoin the main trail in the Bear River valley. The new route cut 85 miles and 7 days off the trip, but it was risky as nearly 45 miles of the new route were without water. The trail gained popularity after it was detailed in a popular guide book published by Joseph Ware in 1849. Ware mistakenly called it the Sublette Cutoff after Solomon Sublette, who had described the trail to him. The route reached the height of its popularity during the California Gold Rush, when the need for speed outweighed risk.
Historians now refer to the route as the Sublette-Greenwood Cutoff in honor of Greenwood.
- Caleb Greenwood K–8 School in the Sacramento City Unified School District is named after Greenwood; it opened in 1950.
- Elk, Mendocino County, California, was formerly called Greenwood after two of Caleb Greenwood's sons who settled there.
- Kelly, Charles, Old Greenwood, the Story of Caleb Greenwood, Trapper, Pathfinder and Early Pioneer of the West. Western Printing, Salt Lake City, 1936
- Hittell, Theodore Henry. "History of California." Vols. 1-2: Pacific Press publishing house and Occidental Publishing Co., 1885/1898 - California.
- "Sublette Greenwood Cutoff". Wyoming State Historic Preservation Office.