Kit Carson (14,165) is the main mountain which includes Challenger Point (14,080).
These mountains offer routes of various levels of difficulty. The most popular ascent is via Willow Creek Trail - Willow Lake (go around to the north - easier) - up the North gulley of Challenger - Summit of Challenger - Saddle between - follow the ramp around the peak and ascend from the south side.
This route begins on the Crestone side at 8,500 feet +/- and ascends steeply on well-groomed trails. (about 5,700 feet of vertical change from trail head to Challenger Point summit). I am not sure of the exact round trip mileage, but it can be done in a day, no camping, in about 14 hours + / -
The climb from the east base of Challenger is steep, but more or less a walk-up.
From challenger to kit carson there is a ramp big enough to drive an 18-wheeler in the summer (without snow). Follow this ramp to a point which seems too far ? down and down, and then, before it ends, turn left (east) and head up to the summit. Some hand holds may be necessary.
HWY 17 to Moffat, CR T to Crestone, take a right at The Main Intersection downtown and follow uphill to the trail head parking lot. Very soon after setting onto the trail (and just before the sign-in station) the trails diverge. Go straight on for South Crestone Lake, to the north, or, cross over the creek (to the south) to get onto the Willow Lake trail. The creek you start along comes from South Crestone Lake.
As you enter the trees on the Willow trail, note the small memorial to Emil, a small stick cross on the left. Emil, apparently, made a wrong turn coming down from Kit Carson / Challenger and fell from the cliffs visible in the photo above. You can see the cliffs just to the left (south) of the gulley on the back of Challenger.
The mountain was privately owned until the recent transfer to the government. The Great Sand Dunes National Monument is now National Park and with that change in ownership there may be change in regulations.
From the Saguache County Board of County Commissioners:
On Friday, April 20, 2007 it was agreed that the County, Forest Service, Park Service, NAT, spiritual centers and Manitou Institute will collaborate to post signage to discourage hikers from trespassing through private property to access Forest Service land East of the Baca.
Thus as of 4/20/2007, posted Forest Service trailheads make for the only legal access.
Even representatives of the CO Mountain Club are going to help get the trespass access points removed from climber websites they have connections with.
When To Climb
May to October. You can expect snow in many places on the ground or in the air through June or July. For the most part July and August are the dry, snowless months.
Excellent camping is allowed just beneath Willow Lake. There are many well-established areas in flat grassy areas and near to water. Camping is prohibited within 300 feet of the lake.
As of Memorial Day 2008: Winter Conditions still exist on route to summit.