Canyons are inherently risky. Flash floods occur without notice on sunny days. Technical skills & surrounding topography knowledge required yet does not eliminate risk.
Much Better Than the Road!!
The one big problem with hiking Caballero Canyon (trail #103) is that above 5800' it turns into more of an open basin wander, leaving the nice cut canyon walls and ambling around in meadows and riparian areas a bit too obviously used by ranchers over the years. Additionally, the ATV use in this upper section continues to be extensive. Trail 103 also goes to the same place as trail #104, Alamo Canyon trail, and if you want to head on up to the higher elevations of the back range, #104 is likely the better choice. Still, the lower section of Caballero Canyon remains a delightful hiking area. Now, with this traverse route added, the exceptional qualities of the hike can be preserved.
This route simply exits the canyon to the north, behind Hershberger Peak, in the drainage immediately to the east of Hells Hole drainage. This is a fairly steep cut, especially in the upper end, but a drainage that provides relatively easy access along the entire length to the old mine site on Hells Hole trail #219. If you are hiking this down from the old mine site, the route is simple... walk past the end of trail sign for #219, past the odds and ends left at the mine, and drop into the steeply eroded wash and head down hill. Continue down hill until you exit the wash, intersecting with the old jeep road portion of Caballero Canyon trail.
Finding your route headed uphill is a bit more involved, but not hard.
Above the 5800'level on Caballero Canyon trail you will exit the narrow canyon and enter more of an huge open bowl. there will be a main riparian drainage winding east and north, and a shorter, steep drainage on the south. The trail follows the northern most drainage. Moving through and out of this very nice stream/forest section, the trail then winds up and over a hill covered with chollo cacti, really a forest of same. You will be able to look up to your left and site the highly distinctive spine of rock strata weaving it's way down the eastern side ridge of Hells Hole Canyon. Your goal is to enter the drainage on the other side of that ridge. You do not want to go up into Hell's Hole Canyon but instead wind your way into the drainage immediately to the east.
It may be handy to study the pictures for this hike to make certain of your route; there are a few minor splits where you could angle up the wrong cut, although it might not really matter. The nice thing about staying in the right cut is that you will end up exactly at T219, and you'll get to enjoy a really delightful little canyon. There will be nice vistas, pleasant mini-falls, some minor sculptured and carved rocks... and depending on the time of year, some interesting water formations, including a side seep spring.
The entry to the drainage is simple and very well marked, in it's own way. Exiting the cacti forest, you begin to wind around and down hill on the jeep track. Looking left, you will see an old water pipe trellised across the wash on your left. Walk under that pipe and into your canyon. Not too far up this cut you will encounter a fork... take the right hand cut, around and behind the VW Bug size white boulder. The hiking gets really nice from this point; enjoy the small falls and sculptured rock.
Your next fork has some of that old pipework strewn about... take the left hand cut this time. Do not pass under the old pipe works crossing the drainage on your right. That pipe is headed up to siphon water from the spring you'll soon encounter, a very interesting side seep.
You will eventually wind your way up to the only real bit of blockage, a small falls that can be climbed or skirted (on the right on the many elk trails there.) The cut stays interesting, with a variety of nice rock structures to enjoy... eventually turning into more and more loose dirt/rock... until you eventually pass under a barb wired fence, indicating that you are near to the old mine works. Move to your left once at the mine to access trail #219.
This traverse avoids having to hike up to Forest road 90 (West Side Road) and the walking along that road to make a connection with all of the Hershberger Peak and Ortega Peak routes. It allows for some nice variety of looping or would really make an out and back up Caballero Canyon to Hershberger Peak a very viable option. It would also make a great hike just for itself... it is well worth the effort to find and explore!
Note: the lower access for this hike is reached by hiking Alamo Canyon trail (#104) up to Caballero Canyon trail (#103)... then following it up drainage to the area noted above... these trails are mostly canyon bottom washes, except for a few places where the trail moves up and onto a side bench. The first notable bench is at the terminus of Caballero canyon, where instead of walking up into the canyon cut, you continue on up Alamo canyon and access the bench trail around the corner. This avoids a waterfall feature, but it is more fun to just stay in the bottom and work your way around the waterfall... your choice.
WARNING! Hiking and outdoor related sports can be dangerous. Be responsible and prepare for the trip. Study the area you are entering and plan accordingly. Dress for the current and unexpected weather changes. Take plenty of water. Never go alone. Make an itinerary with your plan(s), route(s), destination(s) and expected return time. Give your itinerary to trusted family and/or friends.