The Jolley Trail takes its name from a longtime New Castle family who raised sheep and lived on the land the trail now crosses. In 1919, the Jolley Brothers—Herb, Malcolm (Mack), Henry, and Lee—came from Kanab, Utah, as some of the first sheepmen in the New Castle area and formed the Jolley Brothers Sheep Company, at times running as many as 20,000 sheep. Mack Jolley settled on a ranch on Elk Creek at the north edge of New Castle, and that ranch is still owned by his descendants. Henry Jolley settled on a ranch in the Glenwood Springs area that is still owned by his descendants. Lee Jolley returned to Utah. Herb Jolley built his home on ranch property stretching from the east end of downtown New Castle to the New Castle Plaza (City Market) and south to the Colorado River; in 1998, the original ranch house was moved from that property to South E Avenue. The Jolley family has long been and remains an important part of New Castle and Garfield County. Malcolm (Mack) Jolley is the grandfather of New Castle residents Kent and Brett Jolley, and Herb Jolley is the grandfather of Rifle residents Terri Jolley Potter and County Commissioner Mike Samson. The trail was constructed by Roaring Fork Outdoor Volunteers on October 4, 2014.