(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 Colorado 17 to the town of Moffat. On the south side of town, look for a sign for the turn to Crestone. Turn east on the "RD T" road. You will soon see a Forest Service sign that says 15 miles to the South Crestone trailhead. Drive 11.4 miles to a road junction. Keep left and follow the main road into Crestone. In Crestone, turn right (east) onto Galena Street and the road will turn to 2WD dirt, with approx. 2 miles to go. When the road enters National Forest, it is labeled as the "South Crestone Road 949" and becomes more difficult but good-clearance vehicles should be able to make it to the end.
Follow Challenger Point - Route #1 to the summit of Challenger. From Challenger, you can't miss Kit Carson - Photo #1 and Photo #2. Descend east to the small, 13,800-foot saddle between Challenger and Kit Carson (Photo #3) and climb onto a Class 2 ledge called Kit Carson Avenue that runs south along the side of the peak. Continue up the avenue (Photo #4) to reach a small, 13,960-foot saddle between Kit Carson and a large fin called The Prow (right) - Photo #5.
From here you can see the next part of the hike - a longer section of the Avenue which descends east - Photo #6. Hike down the Avenue and pass through a wide notch - Photo #7. Photo #8 looks back on the upper half of the Avenue. Past the notch, Columbia Point (13,980') comes into view, to the east - Photo #9. Your next goal is to locate the entry point into a broad gully which leads toward the summit ridge, before a rock rib near the saddle between Kit Carson and Columbia Point - Photo #10 and Photo #11. Near 13,650', Turn left into the wide, shallow gully - Photo #12 and Photo #13. STOP! Before you leave the Avenue, look around and become familiar with the area so you know how to return to the Avenue on your descent.
From here, it's approximately 450' to the summit. Hike up the center of the gully (Photo #13) on mostly Difficult Class 2 terrain. If the terrain seems very steep, you may have left Kit Carson Avenue too early. Photo #14 shows the terrain above the Avenue. As you climb higher in the gully, you will likely encounter a few sections of easy Class 3. Look for brief trail sections and small cairns as you take the easiest path up the center - Photo #15, Photo #16 and Photo #17. As you approach the ridge crest, angle left and pass through some final rock-outcroppings - Photo #18. Now, just below 14,000', the terrain opens up and the summit is up to the left - Photo #19. Continue to the summit ridge (Photo #20 and Photo #21) and up to the summit - Photo #22, Photo #23 and Photo #24. Taken from Crestone Peak, Photo #25 shows the upper route.
This is the easiest way to climb Kit Carson, but it's a lot of elevation gain in one day. Consider a camp just below Willow Lake. IMPORTANT: This route enters the Sangre De Cristo 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.