Skiing Pikes Peak (Click to enlarge map/pics)

Pikes Peak has several skiable slopes, mostly on the northern slopes facing Woodland Park.  Devil's Playground, a large cirque located directly above Glen Cove, provides excellent road-served skiing whenever the toll road is open above Glen Cove.  Other slopes, particularly the north face Y and Railroad couloirs, offer steep expert runs with a nice hike to get out.  Stay away from these unless you routinely huck big air on double black runs at Crested Butte.  Also be aware that people die most years from skiing-related accidents on Pikes, including avalanches, falling down icy slopes without self-arrest gear, and pure stupidity (snowboarding off 250' cliffs, etc.).  This is adult skiing, so if you don't feel comfortable, volunteer to drive for the skiers and don't put anyone else (or yourself) at risk.

A few links on skiing/alpine climbing on the Peak:
Climbing Railroad Couloir
Climbing the Y Couloir

Glen Cove, the normal winter road closure, is located at about 11,500'.  It's probably best not to try skiing above this until the road is open due to avalanche possibilities, but feel free to prove me wrong.  The lower parking area for Devil's Playground (cars can be safely left here) is at 11,680' and is quite obvious, about 1/4 mile past Glen Cove.  It's best to have your own transportation set up here, but it is still possible to skin up, hitchhike (not condoned but permitted; the rangers' Suburbans sometimes stop also), or carpool with other skiers.  Walking up the road is not allowed, and it usually only takes a few minutes before someone stops for you anyway (Often to ask, 'Are ya'll crazy or something?').
The map (above) shows fairly clearly the Devil's Playground ski runs (in order, from the upper parking at 12,800', the Bowl, 3 Little Pigs/W's, Chimney, Little Italy, Rock Garden, and Cornice).  Asterisks denote the more advanced runs (read:  better than expert level).  Bowl is the easiest run, Cornice the most dangerous, and the Pigs start out as very hard on the (near) easternmost and get more difficult on the (far) westernmost.  With decent snowpack, Chimney and Little Italy are the most fun runs and usually have the best snow conditions.

Skiing the Bottomless Pit routes is more ambitious; I'll refer the reader to Louis Dawson's Guide to Colorado's Fourteeners, Volume 2, for detailed descriptions of the climbing and skiing routes.  If you have a weekend and there's good snow (usually from mid-May to mid- or late-June), there's plenty of other routes not on the maps that you can hike to and ski (not car-served, though).  Just start looking when you're up around Devil's Playground parking.  If anyone else has anything on this online, won't someone let me know?  Thanks.

The Pikes Peak toll road is open year-round, weather permitting, but usually past Glen Cove until late spring.  The toll is $10US per person; the vehicle summit pass is valid for two consecutive days.  Also available is an individual season pass for $50US.  Hours of operation for the toll road are Oct-Apr 0900-1500 and May-Sep 0700-1900 daily.  You cannot stay up on the road after these hours (ie, no car camping).  For more information on the road and closure point, call the rangers at 800-318-9505 or 719-385-7325.  More information (in general) can be found at the Pikes Peak website.