Big Bend Conservancy
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You will find a great deal of discussion on this very subject in various threads. Look up the current one on food storage. What people think of the OML depneds upon whom you ask and what their relevant experience is. Depending upon your level of experience and fitness the OML can be anything from a kind of long dayhike to impossible. There is considerably less vertical on the OML than there is on many Guadalupe hikes, but the hikes down Juniper Canyon and up Blue Creek Canyon are fairly demanding. Coming into the park at the time you are, there should be no problem driving in to a site in the Basin Campground, and you can get your permit at the Basin Ranger station in the morning. Your itinerary has a serious problem, which is the complete unwillingness of the BIBE staff to accommodate people like you. You know your itinerary, you probably will arrive after business hours and want to start your hike before business hours on Thursday. You are not allowed to. You must go to the Panther Junction visitor center or Basin ranger station on Thursday morning to get your permit. You will not be able to start hiking until after 9:00 AM if everything goes well. If you can get to the park before 6:00 PM on Wednesday you can get your permit. Then you can camp at the Basin and hike out as early as you see fit.
Day 1 is perfect. I am a bit unclear on one thing. Are you going to hike up Boot Canyon and loop around on the South Rim to NE4, or stay on the main trail past Boot Spring directly to NE4?
Day 2 is a very short day compared with the other three. If you are planning to hike directly to NE4 then follow the South Rim around to the junction with the Boot Canyon Trail, and back up to the Juniper Canyon Trail and head down. I think you will find that zone camping is much preferable to camping at the car camping site in Juniper Canyon. Hike three miles west on the Dodson Trail and camp just past the saddle at about 4,490'. You will find water in that drainage.
Day 3 go on past Homer Wilson Ranch to somewhere around Cedar Spring. You are unlikely to find water there. But I do like feel of camping in the canyon there. It also shortens your hike out.
Day 4 it is very doable to hike out to the Basin from here. Day 4.5 it is not an option to camp at Laguna Meadow unless you get permitted to do that in advance. Get your permit for four nights and bail if you want to. Don't extend your stay in the high Chisos or they may decide to charge you a considerable amount of change! From Laguna Meadow (get an LW campsite) you can drop into upper Cattail Canyon and get water at the springsless than two miles in.
You are in for a great hike. Not as strenuous as most Guadalupe trails, but a good survey of some of the great terrain in the park, and a good workout for most anybody.
Oh, and as for water:Boot Spring (specifically, a small pipe below the research cabin)Juniper Spring (overgrown but sometimes available downstream from it)Fresno Creek (should be flowing very nicely)Your cache at Homer Wilson RanchExpect to carry at least a gallon per day for your own use at any fill-up point, and don't rely on Juniper Spring for water -- should be top-off only. From Fresno, you can take enough to get you to the ranch cache. This way you provide the bulk of your water and leave more for the wildlife which depends on it where they find it.
I spent six days doing an extended version of the OML over thanksgiving and the only advice I have is pants, long pants. I did it in the opposite direction that you will be going and finished out with a night at NE4, very cool spot.
You will need to have some map reading skills to find the spots where there is water. There are no signs, but the area around the cabin at Boot Spring, the cut-off to Juniper Spring and the spot where Fresno Creek crosses the trail are all fairly easy to find. If you cannot find your own cache at Homer Wilson Ranch then the others might be really hard! From the LW sites the drop into Cattail Canyon is pretty easy as well. Go downstream until you reach water. Go back upstream until you get back to camp.
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