Map of the trail with major landmarks labeled. Google Earth tells me the orange line is 2.85 miles long.
1. La Cueva to gate (~20-30 min)
Just take the trail around the North of La Cueva.
2. Gate to Yellow Rocks (~45-60 min)
Ignore the trail sign for the trail leading to the waterfall. Go straight instead. The trail will feel like it's leading too far NW for a bit but after a lot of meandering it will head straight for the Yellow Rocks, which you'll be able to see. This section of trail is far from straight and occasionally goes over boulders. I call it the "desert maze". Follow cairns and back up if you lose the trail.
3. Yellow rocks
This is the customary location for the first big break of the day.
4. Yellow rocks to Grey Eminence (~15-30min)
Walk southish through the little forest below Yellow Rocks, and mount the next whelt south. Head straight up toward the big dark rock formation. This is section is pretty miserable... first taste of loose/crumbly/slippery trails to come.
5. Grey Eminence to Juniper Saddle (~15-30min)
Go left from the base of this rock formation, and follow the trail around it's NW edge. Stay out of big scree piles (rock slide danger!)... the trail goes over them, not up them. Most of this section is very steep, and you'll be pulling yourself up via trees and rocks along the way.
6. Juniper Saddle
Another good place for a long break, and/or golfing (if you're Jason Jackiewicz). You can look up at Organ Needle from here and spot your next goal - the big pinetree at the entrance to Dark Canyon. (not the very green pinetree to the right... the slightly deader looking one to the left).
7. Juniper Saddle to Slab (~10-20min)
Head north up the hill toward the south facing wall, and follow the trail that hugs the wall (if you're far from the wall, you're off trail). After a while this trail drops down a bit, and you find yourself on a rock slab ramp heading up the mountain. Go up the slab, getting good calf workout, and eventually exit slab to the left, once you see the trail.
8. Slabs to big pinetree (~15-30 min)
Great place to get lost, but don't! The trail splits multiple times before the Big Pinetree, and at each split, both ways work. Just keep going up the fucking mountain. You will need to do some scrambling, and a bit of bushwacking.
9. Big Pinetree to Hummingbird Saddle (~15-30 min)
All trails eventually converge and you end up in a forested gully that becomes increasingly narrow as it goes up. You'll know you're in the right spot when you start seeing tent worms (gross!) and on the trees around you and stinging nettles along the trail.
10. Hummingbird Saddle
From here you'll be able to see White Sands, Sugarloaf, etc. to the east. On a clear day, you can see the Dunn Solar Telescope and APO 3.5m telescope on the distant ridgeline due east.11. Hummingbird Saddle to Organ Needle (~20-30 min)
Follow the trail leading down to the east from the saddle. It stays pretty close to the rock on your left. You will pass not one, but two gullies that lead up toward the summit to your left. The first gully is a 4th class route to the top that I highly recommend for confident climbers. I've never checked out the second gully. The third gully has a deformed, dead Agave in it's back corner, and a crack/ledge system leading up just right of the Agave. This is the "exposed 3rd class scrambling" part of the hike - about 15 ft of it. It is super easy, so don't give up here. Once up the crack thing, hike left until you can't go higher!