(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.
Drive to Aspen and locate the start of to the Maroon Creek road at a roundabout just west of town. Measuring mileage from there, drive 3.2 miles where you'll pass a ranch - this is where the road is closed in winter. At 4.7 miles, reach the entrance station to the park. During summer, there are restrictions to general travel on the Maroon Creek road. The road is closed to cars during the day (people ride buses to reach the lake) unless you are an overnight hiker. Overnight hikers are allowed to proceed any time of the day. Continue to the end of the road at 9 miles. If you're hiking in for a high camp, there's an overnight parking area on the left. The Crater Lake trail starts near Maroon Lake.
Follow the Crater Lake trail along the right side of Maroon Lake (Photo #1) and enter the forest. As you ascend into Maroon Creek, you'll get a preview of the lower route on Pyramid - Photo #2, Photo #3 and Photo #4. Before reaching Crater Lake, turn left onto the Pyramid trail in a flat area just below 10,200' - Photo #5. Hike southeast across a flat, rocky area to reach a small talus field at the base of a 1,000-foot slope. In 2006, the Colorado Fourteeners Initiative (CFI) constructed a sustainable trail up this slope. While climbing the slope, Photo #6 is the view down to Maroon Lake. Near 11,400', reach the entrance to the amphitheater.
Without a maintained trail, continue south into the amphitheater along the right side of a rock glacier - Photo #7 and Photo #8. Hike less than 1/2 mile toward Pyramid's north face before turning left (east) toward the center of the amphitheater - Photo #9. Hop across talus toward the steep slope (Photo #10) below Pyramid's northeast ridge and locate a trail at the base of the slope - (Photo #11).
You must now climb 1,000' to reach 13,000' on the northeast ridge and portions of the slope are loose and scree-covered - Photo #12 and Photo #13. Reach the 13,000-foot saddle on Pyramid's northeast ridge where much of the remaining climb is now visible - Photo #14. Turn right (southwest) and follow a small trail along the right side of a gendarme (Photo #15) and to a small saddle near 13,100' - Photo #16.
The remainder of this route description was assembled from notes taken during multiple summer climbs. The remaining 1,000' requires Class 3 and 4 climbing and careful route-finding but you should find plenty of helpful cairns along the way.
Briefly follow cairns along the right side of the ridge until the terrain becomes more difficult. Climb left onto the ridge (Photo #17) and over to the south side - Photo #18. Below the ridge crest, follow cairns over a couple of small rock ribs and a small gap (Photo #19) to reach a narrow ledge ("cliff traverse") which crosses above some steep terrain - Photo #20, Photo #21 and Photo #22. Photo #23 is a broad look at the area from a bit higher on the route. It's an easy ledge but care must be taken while crossing a narrow section in the middle. After the ledge, follow cairns along the slope, across a small gully (Photo #24), and left to another rock rib. Climb around this rock to reach a steep wall of greenish, light-colored rock - Photo #25 and Photo #26. Climb a few hundred feet up the greenish rock (Photo #27 and Photo #28) and, before reaching the ridge crest, look for cairns to the left. Photo #29 and Photo #30 show some of the steep terrain above the greenish rock.
The remaining 500' to the summit is complex, but usually well-cairned. Continue left of the ridge crest and zigzag up loose, red rock. You will likely encounter a couple of short, Class 4 pitches on the last few hundred feet below the summit. Photo #31, Photo #32 and Photo #33 show some of the terrain. Near 13,900', if you've followed the most direct route, the slope eases near the summit - Photo #34. Photo #35 looks back on the ridge and Photo #36 looks south from the summit. Photo #37 and Photo #38 look west to the Maroon Bells.
This is the standard route on Pyramid but it's difficult and dangerous. 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.