1st time backpacker - need trail!

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I'm hoping to do my first backpacking trip next weekend with my brother (an experienced backpacker, but unfamiliar with the area trails). We'd like to do just a weekend overnight, maybe 10 miles each day. We're based in Portland, but are willing to drive up to 4 hours for a really good trip. Any suggestions? We're both in good hiking shape, so strenuousness isn't a big concern. Thanks for your recommendations!

it's a little late but if you get a chance to introduce someone to the eagle creek trail by the bonneville dam in the gorge you should. it is always way impressive to people even experienced hikers. lots of waterfalls even walking under a waterfall and a super deep beautiful eagle creek gorge. it connects with several other trails including the pct so you can take for as long as you like. try going on weekdays, however, the first few miles can be pretty popular.
Last weekend I visited Surprise Lake (and the alpine country above it) and it was great. It's located in the Goat Rocks Wilderness, about 3.5-4 hours from Portland. I'll try to get a description and photos up as soon as I can.
You may think about trying something around Mount Jefferson. I myself have not done anything in the wilderness area but have been meaning to for years. check out this hike: http://www.trailsnw.com/hikedescription.php?hike num=79 It should be a good one with views and lakes and wildflowers. If this is too short I'm sure that there are a lot of other side trips you can make to add a little length. Have a great time on your hike wherever you end up!