Caleb Greenwood is thought to have been born in Virginia (today West Virginia) early in 1763. We do not know for certain because the early census records were destroyed when the British burned Washington D.C. in 1814. According to third-hand family tradition, Caleb shot a sheriff in 1781 and fled to Tennessee. Based on his own recollections as told to others, he started working in the fur trade in 1808. We know that he was associated with trapping expeditions organized by the Astorians in 1810 and by Manuel Lisa in 1812-1813. In 1815 he was trapping on the Arkansas River without the required license, but after that we know nothing about what he did for the next few years. Late in 1821 or early in 1822 Greenwood was on his way up the Missouri River probably in the employ of the French fur company of Berthold, Pratte and Chouteau. It is thought that he deserted the French company and joined Andrew Henry in 1822 to go on with him to trap the Yellowstone as a free trapper. It is not known whether he participated in the June 2, 1823, battle at the Arikara Village, but he very well might have done so. He may also have been in the Henry party when Hugh Glass was attacked by the grizzly bear.
In 1824 Henry returned to St. Louis and a group of the trappers who had been with him, including Greenwood, crossed South Pass and continued trapping on the eastern slope of the Wind River Mountains. This group was led by John H. Weber. Weber's party went on to Soda Springs (and may have been the ones to name it) and then proceeded to Cub River, tributary of the Bear River, where they established their winter camp. Jim Bridger was in the party and it was from this camp that he ran the Bear all the way down to the Great Salt Lake. On May 23, 1825, Weber's party, in concert with a group led by Jedediah Smith, confronted a group of Hudson's Bay Company trappers led by Peter Skene Ogden. The Americans claimed that the British were on American soil and demanded that they immediately return north. (At the time they were in Mexican Territory.) They encouraged the HBC trappers to join them and offered to purchase any or all of the Ogden party's pelts. The next day twenty-three Hudson's Bay Company men with seven hundred beaver skins deserted to the Americans. Ogden retreated north with the remainder of his party. In July 1825 all of the trappers in the mountains attended the first great rendezvous on the Green River organized by William H. Ashley. We know that Caleb Greenwood was there because Ashley's diary records that he sold him coffee and sugar and bought 202 pounds of beaver from him.
After rendezvous, Greenwood next appeared in the records of Fort Atkinson at the end of November 1825. In December he returned to the mountains and took a Crow Indian woman as his wife. The Greenwood family records indicate that Greenwood's bride was half French and half Crow Indian. Her name was Batchicka Youngcau. It appears that, after marrying, Greenwood lived with the Indians for a number of years, but little is known about this period of his life. One second-hand account indicates that he lived with the Gros Ventres and the Manadans. It is also believed that he and his family may have left the mountains in 1834 after an altercation with Sioux Indians. After that he is reported to have lived for a time on a small farm in northern Missouri. Caleb and his wife had several children before Batchicka died in 1843. The eldest son, John, was born in 1827 or 1828. The second son, Britton Bailey, was born between 1827 and 1830. The third son, Governor Boggs, was born between 1834 and 1836. A fourth son, Willaim Sublette, was born in 1838. A fifth son, James Case, were born in 1841. It is not known when their daughter Angeline was born. A second daughter, Sarah Mojave, was born in 1843 just seven months before her mother died. Batchicka was buried in St. Louis.
In 1841, The Bartleson Party of emmigrants became the first to cross the Sierras into California via the Sonora Pass. In 1843, the Joseph Chiles Party, guided by Joseph Reddeford Walker, crossed the Sierras into California via Walker Pass. In 1844 three parties were organized.and Caleb Greenwood was guide for the Stephens-Townsend-Murphy Party as far as the Rocky Mountains. John and Britton Greenwood were also members of the party. Greenwood's wagon train managed to get ahead of the Ford Party (with Jim Clyman as guide) and the Giliam Party and crossed South Pass in good time and without incident. After crossing the Rockies, Issac Hitchcock guided the party on a supposed shortcut that nearly resulted in disaster, but they managed to get through it with only a few cattle lost. (This shortcut later came to be known as the "Greenwood Cutoff" and still later as the "Sublette Cutoff.") At Fort Hall the party broke into two groups: one bound for Oregon the other for California. On September 3, 1844, the three Greenwoods went with the eleven wagons in the California party. They reached the Carson Sink in October and, guided by a friendly Paiute Indian, "Chief Truckee", made a difficult crossing of the Sierras via Donner Pass with their wagons. In places they had to unload the wagons and hoist them up sheer cliffs with ropes. It was the first time that wagons crossed the summit of the Sierras.
Heavy snow forced the party to divide into two groups at the headwaters of the Yuba River. The three Greenwoods and fourteen others struck out for Sutter's Fort on foot while the remainder of the party stayed with the wagons. Supplies were obtained at Sutter's Fort and men returned to help the remainder of the party to continue on to the fort. Shortly afterwards Greenwood and his two sons were recruited into the force that Sutter organized in support of Governor Micheltorena during the Alvarado Rebellion. On February 21, 1845, the Governor capitulated and Sutter was captured and jailed for a few days. Greenwood and his sons returned to Sutter's Fort and were hired to guide a small party back across Donner Pass to Fort Hall in May 1845. They reached Fort Hall on June 20, 1845. In August 1845 the John Grigsby wagon train, with Greenwood as guide, left Fort Hall for Sutter's Fort via the Donner Pass. They, as well as a number of other wagons which followed in their wake, arrived at the fort in September. Greenwood had found a route up the east side of the mountains that was easier than the one followed during the 1844 crossing.
In 1846 the three Greenwoods lived in the Napa-Lake County region north of San Francisco Bay. In April 1846 Greenwood and his sons, accompanied part way by James Clyman, travelled back across the Sierras to Fort Hall. At the time Greenwood was in his eighties and had long been referred to as "Old Greenwood." In 1846 Charles M. Imus captained a wagon train that traveled from Illinois to California. Greenwood guided the party across the desert, but Truckee guided them across the mountains to Sutter's Fort. Precise data is not available but it would appear that Greenwood brought the rest of his children to California in 1846. It is also interesting to note that the character of the flow of settlers into California changed in 1846. Here-to-fore the emigrants had been tightly organized into a single train that travelled together. In 1846 smaller groups of wagons moved together and followed one another along the well marked trail. This change made it harder for a guide to obtain a decent fee for his services. Greenwood and his sons returned to their hunting and trapping north of San Francisco Bay. When war with Mexico broke out John Greenwood enlisted as a private in Captain John Grigsby's Company E. He served from October 30, 1846, until April 10, 1847.
The Donner Party tried to make it across the Sierras during the winter of 1846-1847. Old Greenwood, at the age of eighty four, volunteered to be part of the second relief party. When the horses were unable to go any further he and his young son, William, remained with the animals while his older son, Btritton, continued on with the relief party. After the Donner tragedy we again loose track of Old Greenwood, but it appears that he may have participated as a guide in the 1848 emigration to California. Gold was discovered at Coloma in January 1848. On their return to California that year Old Greenwood and his older sons made their way to Coloma. By April 1849 the entire Greenwood family was living in one of the mining camp's eighteen log cabins. In June 1849, while living in Coloma, Old Greenwood claimed to have seen an enormous amount of gold near Truckee Lake. This touched off the futile "Greenwood Rush." This appears to have been the origin of the "Gold Lake" fable. Shortly after that the Greenwood family moved to Greenwood Valley. Old Greenwood died sometime in 1849 or 1850.
After their father's death the Greenwood children lived in various parts of northern California. John made Bolinas his home for a while and his brothers lived and worked in Mendocino County at Big River and Cuffy's Cove. Britt, William Boggs and James Greenwood founded Greenwood (now known as Elk). William Sublette and James settled further north in Humboldt County.