Park at the first switchback after passing the Glen Cove souvenir shop, and follow the old roadcut up into the cirque. If you follow this road all the way, it will take you to the sandpit/quarry in the center of the cirque. However, if you contour off the road to the right, you can avoid this feature and begin skinning towards Little Italy.
Glen Cove is an ideal location for tree-skiing and practicing your ski mountaineering skills. In fact, the Pikes Peak Alpine School often runs avalanche and mountaineering courses on the gentle slopes below "The Chimney