hood river is about 40 minutes away from the east side of the mountain, which isnt open in the summer. its about an hour away from timberline, which is open in the summer. hood river is an awsome city on the columbia gorge with cool people, great views, and it is commonly refered to as "windsurf city, usa".
Government camp is the closest city to timberline. it is at the base of the mountain and it a 5 mile drive from the actual resort. hitchiking from govy is very common. govy is small and expensive, and it is filled with skiers from all around the world. street drinking is a popular passtime because it is on a national forest, so its legal.
about 20 minutes down the road towards portland is a bunch of small towns such as zigzag and welches. this is where pollard lives, and it is also very close to windells camp. properties are cheaper and quieter here, but there isnt as much nightlife.
there is also great camping all around hood, which is a very cheap way to go. a great place to camp is trillium lake, which is 3 miles away from govy.