There are so many breweries from Portland to the Dalles. Where ever you're staying you can plan on having several nearby.
Long hike that is basically straight up - but worth the effort!
Drive up to the top or hike a lower trail. Amazing views, rolling foggy hills at the top. you can get a drink at the lodge, recall The Shinning while you're there haha or even go snowboarding! Yes in September. There are a number trail hikes to do with the mountain as the backdrop.
Oregon's most iconic falls. This is a great one to do with children or for anyone who doesn't want a long hike. Tallest Falls in Oregon and easy to get to.