(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 69 south from Westcliffe. Drive 4.5 miles and turn right on Colfax Lane. Drive 5.5 miles to the end of Colfax. Turn right and drive 1 mile on a dirt road to a junction. Continue straight up the 120 Road for 0.3 mile to the Lower 2WD Trailhead at 8,800'. To reach the Upper 4WD Trailhead, continue 2.7 miles to parking/camp spots before the first river crossing, near 9,950'. In 2009, the South Colony Lakes road was permanently closed here (gate) and this is the current trailhead. The trail starts next to the trailhead kiosk, in the parking area.
This is not the standard route on Kit Carson Peak but it's a fine way to climb Kit Carson from the South Colony Lakes area. Just be aware that it's a tedious route, with some Class 3 & 4 climbing and plenty of elevation re-gain.
From the gate closure at 9,950', pass the trailhead sign, cross the foot bridge and walk 2.5 miles up the old South Colony Lakes road to reach a signed junction. Turn right to follow the standard Humboldt Peak trail through the forest - Photo #1. After 0.6 mile on the trail, cross a rocky area - Photo #2. After nearly a mile on this trail, exit the trees and continue through willows to the north of Lower South Colony Lake - Photo #3. Continue toward Upper South Colony Lake (hidden) and locate a trail junction above the lake - Photo #4. Turn right and continue on the Humboldt trail as it zigzags up a steep slope to reach 12,850', on a saddle just west of Humboldt Peak - Photo #5.
Walk west along the ridge to reach the base of a 13,290-foot point and hike nearly 400' up the somewhat-loose ridge (Photo #6) to gain the top of the point where you'll have an excellent view of the route ahead - Photo #7. Staying on or near the ridge crest, scramble 0.4 mile along this rugged ridge (Photo #8 and Photo #9) to reach a large, flat area called "Bears Playground" - Photo #10. Enter the playground near 13,100', turn right and hike northwest toward the top of unnamed point 13,799', also known as "Obstruction Peak" - Photo #11 and Photo #12. Avoid the temptation to hike directly up the rocks by hiking north for a few hundred feet before angling northwest toward the ridge. Once on the ridge crest, turn left and continue to Obstruction's summit - Photo #13.
Your next goal is to gain Kit Carson Mountain's eastern summit which is actually made up of two points - Columbia Point (13,980') and a slightly lower one, often called "Kitty Kat Carson." Like Kit Carson's western summit, Challenger Point (14,081'), Columbia was named after a U.S. Space Shuttle accident. Leave Obstruction's summit and continue west down the Class 2/2+ ridge to reach the saddle between Obstruction and Kitty Kat Carson/Columbia Point - Photo #14. Staying near the right side of the large "bowl" on Kitty Kat's east face, ascend steep Class 2 terrain (Photo #15 and Photo #16) for 600' to reach the top, where you'll see the summit of Columbia Point only 0.1 mile away - Photo #17. Continuing west, drop 50' on the south side before ascending to the top of Columbia - Photo #18.
The next portion of the route is more serious and this is a good place to assess the weather to determine whether or not it's prudent to continue. To reach the summit of Kit Carson Peak, you must descend some serious terrain on Columbia, climb to the summit of Kit Carson and then return via the same route. This is not trivial. Taken from Kit Carson, Photo #19 shows the somewhat-complicated descent of Columbia's west side. Notice the large ledge that's detached from Columbia's west face - it's the key to this descent. From Columbia's summit, descend southwest along a narrow ridge and begin looking for cairns - Photo #20. After descending approx. 100' and before reaching a gendarme on the ridge, locate a tiny notch in the ridge, which probably has a cairn nearby. Turn right (Photo #21), drop slightly from the ridge and descend left on Class 3 terrain (Photo #22) to reach the start of the ledge - Photo #23 and Photo #24. Scramble west down the ledge, pass the 1st of three gullies that drop to the left (Photo #23) and continue to a point on the ledge - Photo #25. Scramble over this point to see the next and final point on the ledge - Photo #26. This is where your descent off Columbia becomes more difficult. A 2nd gully descends from this location but there's also a 3rd gully which drops from the other side of the final point. To keep the difficulty at Class 3, use this 2nd gully and descend (Photo #27 & Photo #28) nearly to the bottom of it before turning right and scrambling across easier Class 3 rock to exit into the upper South (Cole's) Couloir, just below the notch/saddle between Columbia and Kit Carson Peak. For some extra fun, you can traverse past the point and into the 3rd gully. Whether you go over the point or descend a bit before traversing to the 3rd gully, you will be forced to make some Class 4 moves. Once in the 3rd gully, descend (Photo #29 & Photo #30) until you are near the bottom and turn right to drop direclty into the notch/saddle between Columbia and Kit Carson Peak. This notch is also the top of the Outward Bound Couloir, which drops to the north. Taken from the Kit Carson side of the notch, Photo #31 shows the descent from both the 2nd and 3rd gullies.
From the area of the 13,700-foot notch, you must now pass a rock rib (Photo #32) which blocks access to the final face on Kit Carson and you have a couple of options: 1) Drop below the end of the rib to intersect the standard route, near the end of Kit Carson Avenue (Photo #33) or 2) angle up from the notch and climb ~80' and scramble through a nifty passage on the rib - Photo #34 and Photo #35. Either way, once you're on the face, intersect the standard Kit Carson route and climb northwest - Photo #36 and Photo #37. As you approach the summit ridge, you can angle to the left, without having to go all the way to the ridge - Photo #38. Gain the summit and enjoy the views (Photo #39 and Photo #40) before returning via the same route.