Pilot Rock is a prominent basaltic spire 14 miles SSE of Ashland, Oregon, and 1.6 miles north of the OR/CA border.
This is a columnar basalt volcanic core that has had its outer covering eroded away over the eons much like the much larger and better-known Devils Tower in Wyoming.
Originally named Emmons Peak for an early explorer of 1841, the name didn't stick and it is now officially known as Pilot Rock. The peak is easily spotted by travelers approaching from both the north and the south, and is said to have been a navigation marker for early pioneers traveling to and from California. This is easily understood as it is prominently visible and today a few mile long segment of I-5 is lined up exactly with Pilot Rock as it passes by the town of Ashland. It is also visible from the Mt. Ashland area and even from as far away as Mt. McLoughlin, 32 miles to the NNE. If you know where to look, it can even be seen from Mt. Shasta.
The rock soars from about 350 feet to as much as 570 feet above the base talus slope and measures about 450 feet north-to-south and about 850 feet east-to-west.
The peak seems to be popular with local rock climbers and a couple of them can be (barely) seen nearing the summit in the signature photo above.
From the north: Take I-5 southbound, a few miles south of Ashland and get off at exit 6. Continue south on the frontage road ("Old Hwy 99 south") crossing under the freeway and find the PCT trailhead sign on the left. (1 1/4 miles south of the start of the freeway exit ramp.) To drive to near the base of the mountain, continue driving south up the hill for another 8/10 mile and turn left on Pilot Rock Road. Follow this for 2.0 miles and find the parking lot on the right. Take the trail 3/4 mile and turn left on the PCT. In another 2/10 miles the trail splits: Take the right hand fork which takes you directly to the NW cleft. This is a class 3 rock climb with a class 4 crux right at the start and isn't too difficult in good weather.
From the south: From I-5 north take exit 1 after crossing the Oregon border and continue on this frontage road (Old Hwy 99) 3.4 miles to the Pilot Rock Road, turn right and continue as per the above. If going to the PCT trailhead, it's another 8/10 miles north on the frontage road and on the right.
Note: Pilot Rock Road is narrow but has plenty of turnouts and wide spots. It's paved with 2 and 3 inch rocks so it's a 15 MPH drive at best.
The PCT route to the base of the peak passes through private land and BLM land so watch out for cows and close the three gates you'll have to pass through. This route is 4.4 miles to the base of the rock and counting the few ups and downs in the trail is about 2,500 vertical feet total elevation change for the round-trip.
Here's a link to another site with some pics of a more difficult way up the rock than I've described!! Hard Way
No red tape! No parking passes, fees, etc.
This area gets as much as 300 inches of snow in an average winter so this could be a good snow shoe trip or cross country trip. Snow will linger in spots until about May, depending on the year and roads will usualy be snowed in above the frontage road sometime from late November on. Much of the trail enjoys a southern exposure so snow cover may be spotty, even in winter.
For my money, I'd stay in nearby Ashland. Lots of good motels and plenty to do. You could car-camp at the trailhead or even set up a tent and no one is likely to bother you, though. This whole area is a mix of BLM rangeland and private holdings. Too many cows for me!
Once the ski season starts good weather data can be acquired from the Mt. Ashland Ski area which lies just 8 miles away and only 400 ft. higher in elevation than the summit of Pilot Rock. Also, weather info for Siskiyou Pass will tell you what you will find at the junction of Pilot Rock Road or at the PCT trailhead. For now, the following link gives a webcam view and current weather data for exit 6 on I-5, at 4,060' elevation: Webcam & Weather