This is one of the quality trad routes on the upper Castle Rock. As is the case with a couple routes here (eg. Angel), the first pitch is the crux while the upper pitch is a low 5th "run to the summit" (well, almost). Different guidebooks give it a different rating, for example David Whitlaw rates it as 5.9+ in his Weekend Rock: Washington (ISBN-10: 0898869846 ISBN-13: 978-0898869842)while Jeff Smoot gives it a 5.10b rating in his Rock Climbing Washington (ISBN-10: 0762736615 ISBN-13: 978-0762736614) book. Having struggled on the finishing moves of pitch 2 (at least the way we did it), I'd lean towards 10b side but go and see for yourself.
Follow the approach directions to reach the base of the upper Castle Rock (Logger's Ledge) - in other words it can either be a 10 minute hike up a trail or any combination of routes on the lower Castle Rock. Once on Logger's Ledge, move to the right side of Jello Tower and look for a sloping ledge/slab system that starts just right of the opening diehdral of Midway
The route can be easily done in two pitches but we broke things up into 3 mostly for rope drag prevention.
Pitch 1: 5.6 (1 move), 40 feet. Just right of the start of Midway, mantle up onto the sloping ledge/slab system and traverse it right for about 20+ feet. Find a convenient spot to belay just before an obvious 12-foot tall chimney capped by a roof.
Pitch 2: 5.9+/5.10b, 50 feet. Move up the chimney and pull the roof on good face holds and (if your hands are on the large side) a good jam. Move up the crack for 20 feet. Here's where we might have messed up - not sure. As the crack ends, we moved left (crux!) via steep face to an obvious bolted anchor (hanging belay). Perhaps moving right and belaying from gear is easier?
Pitch 3: 5.7, 170 feet. From the bolted anchor, traverse back right and pull two 5.7 moves. After that, follow easiest line to the summit. Plenty of gear and the going is low 5th class.
Descent: Hike down the obvious trail from summit back to your packs.