Most of the terrain you are asking for is located in Mary Jane, the sister resort connected to Winter Park. MJ is known for steeper more challenging terrain and will be much less crowded, sometimes it seems like only 1 out of 10 visitors venture into MJ.
You can either start in MJ or ski over from WP.
From WP take the Zypher Express up and ski down Outhouse or Drunken Frenchmen down to MJ. You can also take the High Lonsome Lift over to MJ but you will have to get back to it first.
Once in MJ take the Summit Express lift up to the top and from there you can either head back to the bowls via the Timberline lift or ski down to the base again via some great shoots, you will be surrounded by blacks and double blacks.
Taking the Timberline lift will take you to Parsenn Bowl that has some nice tree runs that are blacks and blues.
Taking Timberline lift, to the top of Parsenn bowl you can also head over to Vasquez Cirque. Blacks and double blacks with trees and shoots.
The cruisers you might want to check out are in WP around the Olympia Express lift. Take the Zypher Express right from the base of WP and head down to it, follow the signs.
Stay in WP for the cruisers, go to MJ for the more challenging terrain.
I would suggest taking a look at WP's web site and print out the maps.http://www.skiwinterpark.com
Make it steep and deep!