(WINTER) HOLD ON! If you don't have much high-elevation, winter climbing experience, be careful in your planning and take a partner. Even the "easy" 14ers (Quandary, Sherman, Grays & Torreys) can be deadly in winter.
Take Castle Creek from the roundabout just west of the center of Aspen. Drive 12.5 miles (paved) to the Castle Creek trailhead. To the right, Forest Road (FR) 102 continues all all the way to 12,800'. Good-clearance passenger cars can drive about 1 mile up this road to reach the dispersed camp sites along the road. If you want to shorten your hike by parking higher, you must have a 4WD vehicle with good clearance. From the lower trailhead parking area, proceed 1.3 miles to a river crossing. In spring and early summer, this crossing is a challenge for some 4WD vehicles. 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. If you drove up this far, there are a few parking spots near the junction. The road gets worse as it ascends into Montezuma Basin all the way to 12,800'.
Follow Castle Peak's Northeast Ridge Route (#1) to the summit of Castle. From the top, Conundrum Peak is clearly visible to the northwest - Photo #1. Begin the traverse by descending northwest down Castle's northwest ridge - Photo #2. As you descend, it quickly becomes clear that the ridge holds plenty of loose rock. Continue down and pass some rock outcroppings along the way - Photo #3. Care must be taken when passing the rocks seen in Photo #4 - if you decide to downclimb directly over the big rocks, beware of large blocks that may dislodge. About half way down the ridge the pitch eases a bit (Photo #5) as you make your way towards the Castle-Conundrum saddle. Photo #6 is a look back at a portion of this rugged ridge. Continue along the ridge crest (Photo #7) and then along the left side of the ridge (Photo #8, Photo #9) to reach the saddle (13,790') - Photo #10, Photo #11.
From the saddle, the route up Conundrum's South Ridge is fairly obvious - stay near the ridge crest and follow trail segments up through loose rock and small ledges to reach the summit ridge. Begin climbing (Photo #12) and you will soon realize that the rock on this ridge isn't any better than the rock on Castle's northwest ridge. Hike up 50', pass a rock outcropping (Photo #13), and continue to reach a flat area on the ridge - Photo #14. Above this area, the terrain gets a bit steeper, but it's still easy to keep the difficulty at "Difficult Class 2." Look for trail segments and breaks in the rocks that provide passage along the ridge - Photo #15. Photo #16 looks down from this area. Continue up through broken rock (Photo #17) to reach the south end of the summit ridge - Photo #18.
Conundrum has two "summits" along the ridge, and the true summit is the one farther to the north - seen in Photo #1 and Photo #18. Hike to the middle of the summit ridge and reach a notch between the two summits - Photo #19. The Conundrum Couloir route reaches the summit ridge at this notch. Photo #20 shows the final pitch beyond the notch - there are a couple of options to climb this final pitch. Drop 50' to the notch, cross the flat area and begin climbing the final pitch - Photo #21. The easiest way may be to climb it head-on and then turn left about half way up, then turn right to reach the summit. Taken from the summit, Photo #22 is the view of Castle Peak and Photo #23 looks back over the gap and Conundrum's southern summit.
For the descent, return over Conundrum's summit ridge and descend back to the Conundrum-Castle saddle - Photo #24. From the saddle, turn left (east) and descend snow or loose rock/dirt towards the small, high basin between the two peaks - Photo #25. Before reaching the low point of the basin, turn left and traverse along the side to avoid losing ground - Photo #26. Photo #27 looks back at the slope. Continue northeast out of the upper basin to reach lower terrain above the end of the road - Photo #28.
IMPORTANT: This route enters the Maroon Bells - Snowmass Wilderness area. Wilderness areas have special regulations and restrictions for party size, dispersed camping, campfires, etc. Also, dog owners should read the wilderness information carefully because some wilderness areas prohibit dogs to be off-leash and/or limit how close dogs can be to lakes and streams. If you have questions about the Wilderness area, please contact a U.S. Forest Service office for the National Forest(s) listed above.