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Central Oregon Adventures and a McMenamins Recommendation?

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We are returning to Oregon to repeat our enjoyable time at Depoe Bay. In addition, we are adding on some time to further explore Central Oregon - we stayed in Bend 1 night and did the Lava River Tube, but felt the area needed more time.

Last time, we did the week in Depoe Bay plus about 10 more days driving a loop covering Astoria, Forks, Redwoods National Park, Crater Lake, Bend, Hood River. Not to repeat those - looking some recommendations for day trips from Bend, as we have 6 nights at Seventh Mountain Resort.

Specifically - some casual hikes, scenic drives, horseback rides in scenic areas, shops with old junk treasures, oddball things. Oh - and way back when, my mother had a beer business in Prineville (in her young wild days), so am doing some research to maybe capture some family history.

We have stayed a night at McMenamins in Bend, but that's not in the cards this time. Have 2-3 extra nights before we need to head home; any suggestions on your favorite Mcmenamins? Maybe wine country or Portland? I am having difficulty picking, they are such a funky concept, so hard to judge and decide.

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