Sisters was established in 1888 when nearby Camp Polk, a short-lived military outpost, was dismantled. Following abandonment of the camp, the site was homesteaded in 1870 by Samuel M. Hindman, who subsequently operated a store and post office.

Sisters is named after its backdrop to the south, the Three Sisters. These over-10,000-foot-high peaks were the last major obstacle for the pioneers to circumnavigate on their journey to the fertile Willamette Valley. The emigrants named the mountains after some of the virtues that helped propel them through the hardships of the frontier: faith, hope, and charity.

Over the years, no one could agree on exactly which mountain was named what, so the Oregon legislature settled the dispute by labeling the mountains as the North, Middle, and South Sisters.

In any case, although most of the Old Santiam Wagon Road has long since been replaced by asphalt and forest overgrowth, the 19th-century flavor has been preserved in the town of Sisters. Wooden boardwalks, 1880s-style storefronts, and plenty of good old-fashioned Western hospitality grace this small town of about 1,600.

Some people are quick to lambaste the thematic zoning ordinances of Sisters as a cheap gimmick to lure tourists, while others enjoy the lovingly re-created ambience and the abundance of charming, independently owned shops.

As well as being a food, fuel, and lodging stop, Sisters is also a jumping-off point for a wealth of outdoor activities. Skiing at Hoodoo Ski Bowl, fly-fishing and rafting on the Metolius River, and backpacking into the great Three Sisters Wilderness are just a few of the popular local pursuits.

Nearby luxury resorts such as Black Butte Ranch, an annual rodeo, a nationally famous quilting event, and a large and scenic elk ranch off Route 242 on the outskirts of town add to the appeal of this vintage village.