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Apr 20, 2024 — The Sheephead Mountain Trailhead is just a pull-off on the side of Kitchen Creek Road at a locked gate. Tyler and I hiked along an old doubletrack past the gate that descended slowly as it curved through the forest, slowly becoming singletrack. We reached a forest road that headed south and followed it, and although apparently this road briefly crosses through private property, we saw no negative signage. The private property portion lasts only for a short time anyway, so we weren't too concerned, but you could hypothetically stay off the road and hike through the forest if you're concerned about trespassing.
We left the road when we noted a small cairn, but the route is a bit unclear at first and we had difficulty sticking to the social trail both on the ascent and descent. After a couple hundred feet of floundering, we located the well-carved social trail snaking through the brush. Without its existence we would have absolutely turned around. It'd be a steep and heinous slope up to Sheephead Mountain if not for the saintly folks who maintain this route. Initially, the route headed up a gully through/below taller brush, but then we emerged into chaparral and sunlight and were forced to move slowly to avoid getting torn up by stray manzanita branches.
We reached the summit area, where the trail continued briefly west to the high point, a stack of large boulders. We kept the ascent Class 2+ on the east side by wrapping around some brush and scrambling up a flat slab to gain the high point. The views from here were really nice, especially toward Cuyamaca Peak.
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Hire/refer me as a web developer or send me a few bucks if you find my site useful. I'm not sponsored, so all fees are out-of-pocket and my time preparing trip reports is unpaid. I really appreciate it!