...Okay, I'm very very reluctant to give out this information... but it is unjust for me not to.
When the snow is deep and soft and the woods are full of snow... head to Timberline. I'm about to tell you some of the most secret lines on the entire mountain (lines I, a 10 year local at Timberline just recently discovered).
Head up Silver Queen and after tower 13 keep your eyes peeled. You should see a slanted tree with enough height to go underneath on the left side of the trail and a few meteres upslope of it a downed tree trailside. Okay, when you get to tower 15 look to your left, far left. Right before Silver Streak steepens there is a tight woods entrance on skiers right (as you head down). Build up some speed and enter here. Pick your way through the tight scrub brush and small trees until the trail begins to open more. Now, look for the big blowndown trailside tree and head to the right before you reach it... in the pine trees. Shred all that powdery goodness. If you are up to it, continue down the trail and work your way to the upper connector between The Drop and Silver Streak. If you are not, look for the slanted tree with clearance to go underneath. Cut left until you go beneath this tree and head back onto Silver Streak. Either way you will end back on Silver Streak.
Now, when you approach the portion where White Lightening merges into Silver Streak look on skiers right for two wooden posts with a CAUTION sign. Take a few turns past the two posts around some tight trees and spot the entrance on skiers right into more glades. You will enter and make a sharp left to avoid a log. Continue on towards the trail between mid-station and The Drop, cross it, and head into the woods on the other side. This is a bike trail and it is fun. You'll come out at the merge of White-Out and Salamander.
Now, head over to The Drop. Immediately after the initial drop head into the trees on skiers left. Stay close to the trail, even when it becomes steep. Eventually you'll go to the right of several blowdowns and connect onto a narrow trail leading you back to Silver Streak. From here you can do the above-mentioned lower glades.
Now, head down Flag Spruce from Silver Queen towards OTW. There is a small entrance into the woods on skiers left before the entrance to OTW becomes visible. Take this and work the entire left-side glades of OTW, which are heavenly, but watch out on the tight entrance. Now, work across OTW towards the big dead (and broken) tree on skiers right. This has a large flat associated with it. Peer into former Cherry Bowl Glades. Pick your line and stay on the high side of the bowl for the best woods skiing of your life. You will come out at the bottom of OTW.
The woods between where Thunderstruck splits by the pumphouse on skiers left are also amazing, work your way towards Almost Heaven, cross Hiz, then work the trees to Herz, continute below Herz and into the woods staying to the left to come out by the water tower. You will need lots of snow for this.
I will not reveal the lines into upper Cherry Bowl... but let's say a little prayer (hint hint) they never get closed-off.
Finally, if you want a truely unique experience, pack-up a lunch and head to the top of the Thunderdraft lift. Take your board/skis off and hike the marked bike trail just behind the Ski Patrol hut. Continue on this trail working essentially off the backside of the mountain. Soon you will reach an open meadow with an amazing view of the southern valley. There's a picnic table (which may or may not have been jibbed
) where you can enjoy your snowy lunch and get in a few foot-access powder turns.
Enjoy!
OH MY GOD!!!! You have given away at least half of the nicest tree runs on Herz Hill. Please Cannaanman, don't share the rest! 
The curse of the flatlanders will follow you forever if you do.
