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Looks like you are in the Blue mountains? I've never ridden there but in general I like to wait at least a month into the heart of snow season before hitting the hills because until that point the rocks and stumps are truly dangerous. Maybe you have some grassy or otherwise smooth hills out there in Eastern OR. In the Cascades it's rocky and stumpy and I always have to wait until the snow on the hills gets significantly deeper than the stumps and gets a somewhat firm base underneath. Once it gets to that point just start going for it and see what your sled and your skills can do. My favorite thing now is diagonal climbing/sidehilling, demonstrated in the video that's in my current signature. Your track isn't a true hillclimber but it can handle a lot of hills, especially in firmer snow conditions it can go just about anywhere, and you have plenty of engine to get you there. The main thing is if you are trying to highmark, go into the hill with as much speed as you can get and do whatever you can to keep momentum. Spring is my favorite time to hillclimb because the base is firm so you won't hit anything that you can't see even if the snow isn't too thick.

Spend the beginning of the season riding around on the trails finding the spots you want to hillclimb and making sure your rig is dialed. Almost all the open areas I ride are either rock quarries, clearcuts, or lakes, and I pretty much don't want to go crazy in any of those areas until winter has truly set in.

How is the riding out there? If you look at my youtube page I make it look like there are a lot of open areas out here in the Northern OR Cascades, but there aren't! And the trail grooming is limited and very sporadic. The best powder and hillclimbing spots are quite a long trail ride away, and then there is never enough gas in the tank!! The only good thing about it is I get 7 to 8 months of snow.
 

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You might try posting on Snowest.com, there are a lot of western riders on that forum that ride your area...
 
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