South Colony or Spanish Creek TH.
As a stand alone destination probably the easiest route is the East Ridge. Proceed to the Kit Carson - Crestone Peak saddle known as the Bears Playground from either the South Colony or Spanish Creek TH.
If coming from South Colony there are two routes.
1) As a spring snow climb only hike directly up the South Colony Lakes basin to its western end and whichever couloir looks most inviting. The couloirs on the NW wall of the cirque top out at the Bears Playground.
2) Humboldt Trail is the second option. Take the very good trail from Upper South Colony Lake at 12,030 to the Humboldt Saddle at 12,850. The route becomes a little intricate here. You need to follow the ridge west. You do not need to climb over the top of the highpoint but you will be close. Begin ascending the ridgeline and look for a light use trail wrapping around the highpoint on the west/nw side. When you reach the north side of the ridge and the trail disappears into all that 'yikes' terrain you have gone just a bit too far. Turn around and walk back a short distance to the ramp you didn't notice before. Hike up and continue west. There are bits of visible use trail. Contour around the high point and follow the ridge crest to the Bears Playground. Between the highpoint and the Playground are several rock ribs perpendicular to the ridgeline that need to be negotiated. Descending below them keeps the difficulty at a loose class 2 - not worth it. Tackle them along the south side of the crest except for one which needs to be crossed through a narrow notch on the north side. Sorry I cannot remember which one it is, however, if you are staying more or less near the ridge crest and the other side of the rock rib looks like class 4-5, look around the north side for that small notch. Difficulty on the ribs is no more than a few class 3 moves at a time. Exposure is limited.
From the Playground it is a class 2 hike up the ridge to the twin summitted Columbia Point. Begin by skirting around "Obstruction Peak"/Point 13799 on the western side. If you look sharp, you will notice a cairned route contouring around the point to the saddle. What you see is actually a false summit, "Kitty Kat Carson". It is not as steep as it looks. Proceed up the trail to Kitty Kat's summit. The westernmost summit is the highest so continue onward with a small descent to a saddle and back up to Columbia Point.
For summer, standard mountain hiking gear is required.
For spring snow season and winter add crampons and ice ax.
Traverse to Kit Carson Peak
If you are continuing on to Kit Carson it looks like suicide but there is a cairned route that keeps the difficulty at a moderately exposed class 3. The trail starts just a short distance SE of the summit. Look for some small cairns and good luck.