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Route to summit both Castle peak and Conundrum from Castle creek trailhead. 3,350’ elevation gain, 8.5 mile round trip depending on actual route taken.

Take Castle Creek from the roundabout just west of the center of Aspen. Drive 12.5 miles (paved) to the Castle Creek trailhead.
Park there for a longer 14-15 mile roundtrip hike. To the right, Forest Road (FR) 102 continues on and proceeds 1.3 miles to a river crossing. Continue another 1.7 miles up FR 102 to a junction. Left will take you up the nasty Pearl Pass 4WD road. Staying right will keep you on the Castle Creek 102 road. There are camping spots right off the road here.

Follow the trail up to the saddle between Castle and Conundrum. Watch/listen for rockfall. You can traverse to either peak from the saddle, then return and nab the other peak.
From the saddle, the route up Conundrum’s South Ridge is fairly obvious as is the line up Castle – stay near the ridge crest and follow trail segments up through loose rock and small ledges to reach either summit ridge.