Backpacking in Oregon suggestions

[pencak]

I'll be in Oregon in July for a family reunion. I figure I could stay a week or so longer and do a 50mi backpack or something like that. I'm pretty sure I can get a ride to a trail head that's a reasonable distance from Eugene, OR. So far I'm looking at:

Timberline Trail Loop - 41mi. 8,100 elev gain, loops around Mt. Hood (might be a little far from Eugene, so I'm unsure of trail head security)
Map igallery/image_page.php?id=4165

Three Sisters Loop - 55mi. 8,200 elev gain, can be crowded in sections and may need special permits
Map igallery/image_page.php?id=4166

Separation Creek Loop - 42mi. 4,200 elev gain, more solitude than Three Sisters buy may not be as scenic
Map igallery/image_page.php?id=4167

What do you think is my best option, or do you have any other suggestions?

[pencak]

I'm starting to lean toward the Timberline Trail loop now that I saw the Mt. Hood summit climb
http://www.summitpost.org/mountain/rock ... -hood.html
Throw that in for a day and it rounds it out nicely. I could go totally leisure and stay a few days in places to make it a good 7 day trip. Unless there are better ideas.

Hey, if I do a summit climb like this I'll need companions. If I can make a decision and narrow down details I'll post it.

[sneakySASQUATCH]

In response to pencak:
If you start at the Timberline parking lot you should be fine. I did ski patrol there for 8 years, several multi day hikes, and mountaineering classes and never had any trouble with my vehicle security. Besides Timberline Lodge is worth seeing when you get done. You will want to park in the climbing lot on your right before you get to the main parking lot for the lodge and ski area. There used to be and probably still is a forest service check in at the lower lodge for back country and summit hiking. I'm not sure about the current reservation or permit process as it's been six years since I have hiked on Mt. Hood. I know they were looking at limiting Summit Groups because there were so many people climbing particularly after the accident a few years ago. Remember the footage of the blackhawk rolling 1200 vertical feet down Hood? Hope this helps. This time of year the loop trail will be under snow so keep that in mind. Also, weather comes in quick so be prepared. Enjoy and post pictures!