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Vista House Overlook, Mt. Hood and Vintage Shopping

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Family and I are headed to Portland later this week (2 adults + 3 kids --- 20, 14 and 10). We'd like to visit Vista House Overlook. How long of a drive will it be from Vista House to Mt. Hood? Also, 20 year old would like to visit a few vintage clothing shops...... Any suggestions?! I've checked suggestions on Yelp but, would like to hear from the Fodor's Community as well.

We'd also like to mix in a visit to a cheese farm ---- Tillamook is a consideration but, I'd like to know if there are better options?

14 year old would like to visit University of Oregon..... Other things to do in the area of that campus or along the way?

Thanks!

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