I have never done much riding in the Chuckanuts so I can't speak to that. I have done a great deal of riding in Anacortes. I lived there for about 9 years. The trails there are really super. Lots of climbing, great singletrack decents, the rain shadow makes it dry-ish, hardly any trail traffic, and natural technical stuff. The donut house for pre ride stuff and the Brown Lantern ale house and Anacortes Brewery for after ride stuff.