Very rewarding 1/2 day "out & back" hike. This hike is a great option if you want to take in the spectacle of Mt Hood without committing an entire day or more to it. The level of challenge is enough that I can't see you getting to the summit of with small children or if you're not in decent shape. The hike doesn't have many steep grades but makes up for it with a consistent steady climb. The summit is just under 5k ft so plan for it to be cool and windy at the summit. The views of Mt. Hood during the hike and at the summit of Tom Dick & Harry Mtn are possibly the best you can get.
Recommend getting an early start to your hike 7 - 8am for a more intimate experience.