Due to lack of info just sharing what I found. I have not completed this hike yet.
This is a scenic ride over rolling terrain through juniper and pine forests and openings between Harvey Gap and Forest Road 3380. The north end of the trail is accessible from the Wildcat Campground by a long (5 mile), uphill climb on a good gravel road to Harvey Gap. The trail is wide and there is the possibility of meeting an ATV, motorcycle, or horse. This eight-mile trail is classified as "more difficult" because of a series of short, rough, steep sections. The return trip to Wildcat Campground is a steep (5 mile), downhill ride on a secondary gravel road (Forest Road 3380) to the intersection with Forest Road 33, then north for 5 miles back to Wildcat.
Read more: http://www.gorp.com/parks-guide/travel-ta-ochoco-national-forest-biking-oregon-sidwcmdev_066510.html#ixzz3lFRRLE6V
Stein's Pillar is a 350 foot tall, 120 foot wide pillar of rock. There are many examples of this type of pillar in Central Oregon but this one in particular was caused when avalanches of hot ash, volcanic dust and pumice flowed into this valley, followed by a long period of erosion that carved it out of the landscape. It is named for the discoverer, who found it in the 1860s. His name, Major Enoch Steen, was misspelled so often as 'Stein' that eventually it stuck. Moving on from the history bit, this is cool hike, passing through some burned areas. This area is plagued by fires due to dryness and lightning strikes. Last summer, the entire forest was closed due to wildfires. But the evidence of past fires has caused an interesting landscape of burned chunks of wood and dead snags, along with all the greenery. Quite a few wildflowers were blooming, which is always a bonus, too. And on a clear day, one can see the Cascades from 100 miles away. Once you reach the Pillar, climb into the grotto-like entrance on the right-hand side of it for views north into the Mill Creek Wilderness. The dog really enjoyed this hike, too, but be aware that there is as much ascent on the way back as there is on the way in. Tip: make sure you continue a mile down Mill Creek Road before turning off onto Road 500 for the climb to the trailhead. There is a viewpoint of the Pillar and an interpretive sign board.
A really neat trail for anyone who loves geological oddities, or for fitness hikers. This out-and-back travels 2.3 miles through thin forest, arriving at a beautiful viewpoint of Steins Pillar, and then descends rapidly (mostly on stairs) for a final 0.3 miles to the base on the pillar. The altitude peak of the trail is in the middle, so there are two sturdy climbs involved. Lots of opportunities for great views, so bring a camera. Expect to see very few other hikers; it's probable you'll have the trail to yourself. About a 30 minute drive from Prineville, including a rough 2 miles off of Mill Creek Rd to the trailhead.
The trail is pretty well-maintained, with a couple fallen trees that will have to be hopped over. Make sure you divert left at the halfway point to the viewpoint for some pictures before returning to the trail (there is relatively new signage at this fork). And when the trail is done and you return to Mill Creek Rd., take a right turn and follow signs to the official viewpoint for the best view of the pillar. Do the trail early in the day as there is high tree cover to the west, and allow 2.5 hours for the total hike.
A great, exhilirating hike with plenty of views and a landmark that all Central Oregonians should see.
Nice hike to the pillars. We went on a beautiful sunny day but there were pockets of snow, mud and ice along the way. The drive up to the trailhead was adventurous as there were spots of deep snow on the narrow road. Well worth the hike to the end. Beautiful views.
Hiked this lovely trail a few times with 13yr old son, two german shepherds, myself and husband. We've hiked this in the wet spring, early summer and even in the winter with snow. Trail can be sketchy in the snow or mud in a couple of areas, but definitely doable. Easy enough elevation gains, and some really beautiful areas. Once you get to the initial pillar, there is an area you can have lunch "in" the rock, and though we have not, some folks do camp overnight. In three trips we have seen one couple with their dog one time, and heard a small group another time. Not highly traveled.