Quandary Peak is probably one of the earliest peaks to be ridden in Colorado.  Every year several hundred riders/skiers climb to the summit and ride it.  There are often 15-20 snowboarders/skiers on the summit at the same time on a busy winter day.  The east ridge provides an avalanche safe ascent/descent route.  You can also drop into the east bowls which provide a fairly mellow ski for a 14er descent.  These bowls, particularly the lower bowl, are avalanche prone though.  A popular couloir descent, called the Cristo couloir, drops off the southern face of Quandary from near the summit.  There is also a steeper, little known couloir on the north side of Quandary called White Widow.  
earliest known descents:
March 1996-Dan Bogardus rode Quandry-east slopes
spring 1996- Barrows Worm and Mark Rikkers-Cristo Couloir  
04/2000 and 04/2001- Erik Kling, Josh Lewis(skier), and Rolf Kelly(skier) descend the eastern bowls.
February 2005- Zach Taylor and Ricardo Contro descend the eastern bowls.
March 2005-Zach Taylor and Casey Flynn descend the eastern bowls
5/15/2005- Jarrett Luttrell descends the Cristo Couloir.  Check out his TR at http://www.14ers.com/php14ers/tripreport.php?trip=5577&parmuser=Easy+Rider&np=3&cpgm=tripuser
05/2006-Zach Taylor, Hammish Gowans(skier) and Mike Bannister(skier) descend the Cristo Couloir.
05/2007-Zach Taylor, Mike Bannister(skier), and Vannessa Logsdon(skier) descend the Cristo Couloir
February 2008-Chapin Johnson and Zach Taylor descend the east bowls
3/1/2008-Nat Burns and Austin Porzak(skier) descend the southeast face of Quandary Peak and link it up to the Cristo Couloir on the lower face.
2/28/2009-Grant Lewis and Zach Taylor descend the eastern bowls.  Check out Zach's trip report at
http://www.zachtaylorsnowboarding.com/events.html .
4/10/2010-Zach Taylor, Joel Paula(skier) and Mike Bannister(skier) climb the east ridge and descend the Cristo Couloir.  Check out Zach's trip report at
http://www.zachtaylorsnowboarding.com/Quandary_Cristo_Couloir_2010.html  .
Quandary Peak 14,265'
Kirill Kireyev hiking up the upper east ridge of Quandary Peak, unknown skiers pictured behind.  February 2005 courtesy of Zach Taylor
photo-Nat Burns on the summit of Quandry Peak, photo by Austin Porzak, 2008.
photo-Nat Burns taking a slide on the southeast face of Quandry peak. photo by Austin Porzak, 2008.
photo- A view of the south face of Quandry Peak from Mt Lincoln.  The East ridge of North Star Mountain is just visible in the foreground.  photo by Erik Kling, 5/19/2005