The Greensprings Highway, officially State Route 66, heads east into the mountains from Ashland on a historic route in use for at least 160 years.
In 1846, Jesse and Lindsay Applegate established a new trail into the Rogue Valley. The northernmost branch of the Applegate Trail became the general route of today’s Greensprings highway. By the turn of the century, the route was a stage coach road with several roadhouses in the Greensprings area. One stage stop was operated by Charles and Lulu Decarlow, who owned a stock ranch nearby.
In 1919, the Oregon Highway Department began construction of the Ashland-Klamath Falls Highway. It followed the stage road, but minimized the steep grades and dangerous turns of the former wagon road. As the main route for vehicles between the Rogue Valley and the Klamath Basin, decades before the existence of Highway 140 east of Medford, the Decarlows saw increased traffic through Pinehurst when the new asphalt highway was completed. They established the historic Pinehurst Inn to serve lunch and coffee to passing motorists.
The Emigrant Creek dam, constructed in 1960, submerged part of the road, forcing the rerouting of Highway 66 around the lake.
Sources: Brown, Ron. "Oregon Trails: Crossing the Greensprings." Newswatch 12. 14 May 2012. Web. 18 Mar. 2015. www.kdrv.com; Most, Stephen. "Inhabiting the Land: The Applegate Trail." Oregon History Project. Oregon Historical Society, 2003. Web. 18 Mar. 2015; United States Federal Census. 1920.