(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.
Once you are near the lake, follow the trail as it parallels the lake's north side. Leave the trees and continue through thick willows along the shore. Your next goal is to gain the cliffs/headwall on the east end of the lake. Before reaching the cliffs, turn left and climb north up the hillside on a rugged trail - Photo #1. Climb 150', turn right and continue through bushes to reach the top of the cliffs, near 11,800', where you get a view of Kit Carson and the approach to the Outward Bound (O.B.) couloir - Photo #2.
Cross the stream and follow small cairns and trail segments across the remainder of this flat area. Above 11,800', angle left through willows and bushes to reach the base of Challenger's standard, north slope route, near 11,900' - Photo #3. Now above the creek, continue southeast toward the base of the cliffs below Kit Carson's north ridge (Photo #4) and continue traversing southeast as 13er Columbia Point comes back into view near 12,600' - Photo #5. Pass under the remaining rocks/cliffs at the base of the north ridge and the terrain opens up as you enter the apron below the O.B. couloir - Photo #6 and Photo #7. The O.B. climbs southwest to reach a tiny saddle between 13er Columbia Point and Kit Carson Peak.
Turn right and begin climbing southwest toward the base of the couloir - Photo #8. Finally, you'll enter the confines of the couloir at 13,000' as the slope angle increases to 40 degrees - Photo #9. From the entrance, climb 700' of elevation to reach the top - Photo #10, Photo #11, Photo #12, Photo #13, Photo #14 and Photo #15. The slope angle probably averages around 43 degrees and may exceed 50 degrees at the top, where you might also find a cornice.
From the 13,700-foot saddle at the top of the couloir, drop a few feet off the south side (Photo #16) and traverse right (west) onto a small rib which blocks your view of Kit Carson's southeast face - Photo #17. Climb over the rib (Photo #18 and Photo #19) and continue west onto the face (Photo #20) to join the general area of the standard, summer route - Photo #21. Taken near 14,000', Photo #22 looks back on the traverse from O.B. couloir. Gain the summit ridge and continue to the top - Photo #23, Photo #24 and Photo #25.