I asked this last year and while we intended to drive up to Skibowl, the day we went there was traffic so we ended up just pulling into a school and playing in a field of snow (which was great for our son who had never played in snow until then). This year we plan to actually make it up to Skibowl. I've googled and tried the old link for the Sandy Starbucks shuttle to Skibowl but I am unable to find a shuttle service to get up to Skibowl.
My son will be 3 and so I think as long as there is tubing or sledding he'd be happy. Any other mountains with convenient shuttles (either out of Portland or some parking lot where we could leave our rental)?
Last but not least, thanks Chinookgrrl, jkoregon & half-Brit. We LOVED our last Christmas trip to Oregon so much we're coming back. We loved Zoolights (went twice), the Cinnamon Bear Cruise (going again this trip), the Grotto (surprisingly the kids REALLY REALLY liked this too) and the Science museum (we go there late so we only had a little over an hour there, we'll go earlier this time around so the kids can play longer). We didn't get to eat at as many food carts as we wanted to, coming from Hawaii the severe cold took us by surprise, it was WAY too cold for us last year...we'll pack more layers this year though.