Sun River or Bend is your best option for all those activities right now.

Horrible choices!

it really depends on when you will be here. The best things to do in the state have a strong seasonal aspect, even with respect to June vs. August because of snowpack, when the mosquitos come (And then go).

Likewise, OR is a pretty large state, easily 8 hours to drive across it. Do you have a generally area in mind or where will you be approaching from, driving from CA, WA, ID, flying into Portland?

Do you want to ride road, gravel or mountain?

I can give you very specific suggestions if you can provide a jist of answer to my questions.

Also, how do you feel about beer vs. wine?

Dunno if it is open or not, but Hagg Lake is the site of local Triathlon races and Xterra races. Road and trails to run/bike, disc golf, etc.

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You could do something like Timmothy Lake up on Mt Hood. You'd probably want a gravel bike. We filmed this video here:
https://www.youtube.com/watch?v=jDECv-R1_Eg

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YouTube

Look into baker city, some good beer there and more quiet and killer climbs on bike, hiking. On east side of state, great town. Anthony Lakes Ski area is good to ride to , mtb on, and hike.

Second Central Oregon. Four good locations to stay and use as a home base are Bend, Redmond, Sunriver Resort, or Eagle Crest Resort. All within 30 minutes of each other and all within a short drive to many lakes and rivers for fishing, trails and mountains for hiking, and you can walk out the front door and complete a 50+ mile bike ride (road/gravel/mountain) without ever having to stop. With COVID, the counties in Central Oregon have already opened up, while the Portland metropolitan area is note quite there yet, and having to manage protesters. While Oregon is a big state, most of the population lives in the Portland area, south along the I-5 freeway corridor, or Redmond/Bend area in Central Oregon. Rest of the state is mostly agriculture.

Ha! Surprised to see my neck of the woods mentioned here...but yeah, the East has plenty to offer.

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We were in Sunriver last week and it was awesome. We were only there for 3 full days book-ended by two 450 mile drives to and from. I recommend spending at least five full days because there is so much to see and do. Cycling up to Mt. Bachelor and encountering a snow flurry was certainly a highlight which can be expected in early June. We played a round of golf, ran the trails and ventured into Bend. All in all it was a great trip despite the cold weather.