Mt. Hood is where families and short tracks go sledding on the groomed roads. Bend has the wild Bend crowd at Mt. Bachelor and Paulina, that has both families and 20 something hard core types. Oregon sledding is pretty boring ordinarily, unless you have 3 feet of new powder. Anything above 4000 feet is going to have enough snow to sled after Christmas. There are a lot of places to explore with no names and no snoparks in the Cascades, that you just wait for enough snow to keep the ATV's out.
Anywhere between St. Helens and Mt. Adams is where the more experienced sledders tend to go. You can get up to 11,000 feet on Mt. Adams. The reservation on the east side of Mt. Adams, is right out of National Geographic. Any thing north of Carson or Trout Lake, is going to be good. Then there is a lot of powder hills horth of La Grande and east to McCall Idaho.