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Hello avid hikers! We have three boys, ages 9, 11 and 15 and my wife and I want to take them on an easy overnight hike. Any ideas of where to get started? We'd like to hike the Columbia Gorge or Mt. Hood area. Thank you!

On the eastside of Mt. Hood there is an area "Bonnie Creek", miles of access roads once you leave the main roads. Sportsman campsites are pretty prolific. Lots of opportunity for day hikes, nice country in the national forest.
Excellent, it's good to see people taking their kids on backpacking trips! I'm not sure how far you want to hike each day, so something like the Timberline Trail would be a good option (of course not the entire trail!). I would just drive to one of the many trailheads (Timberline Lodge, Cloud Cap, etc..), and hike along the trail until you find a good place to camp. This way, you can do as long, or as little of a hike as you feel like, and the scenery will be great. Snow can linger on the trail into late July and early August, so that may be a consideration depending on when you go.
Maybe Mirror Lake. Its a short trail with good scenery, but could be quite busy.