Family Trip to Oregon- Advice?

I spent the last few years living in southern Oregon. If you make it towards Charleston, I would definitely try to get on the Betty Kay for a charter trip. It's an affordable 1/2 day trip and you'll catch your limit of rockfish and lings if you know how to fish. Up around Portland and Mt. Hood... check out Voodoo doughnuts and look for a scenic hike around Mt. Hood, not much else there that interests me. It's been a few years since I was there, the rioting and protest vs. counter protesting seems to have really found a home in Portland since then.
 
Silver Falls is a great hike, east of Salem. Multnomah Falls is pretty close to Cascade Locks, and is a very popular must-see in the gorge. Portland’s Japanese garden is a nice way to have fun outside.

On the coast, the grey whale migration is underway, so bring some binos and BOLO for some blows. Also, not sure about the north coast locations, but crabbing for dungeness is a really fun activity that’s inexpensive. Many places you can just drop your crab trap, go and do something else for a few hours, then come back and hopefully have a pot full of delicious crabs! June’s not exactly the best month for crabbing, but there’s definitely legal keepers you can still catch. Red rock crab, too. You can keep any size, any sex of those.

Not sure how much time you have, or how much traveling you’re up to, but Bend is a great town for visiting. See the high desert, beautiful views of the cascades, and many, many breweries that are worth trying.

Pretty much every winery in the valley is good. All the ones I know are near Eugene, so I can’t give you pointers on specifics near Portland.
 
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Some good stuff here for sure, thanks guys! Certainly going to try and add Tillamook into the day trip to Cannon Beach. Looking into a few more of these as well.

Anyone ever do the riverboat tour out of Cascade Locks?
My wife and I did the dinner cruise from Cascade Locks for our anniversary last year. Beautiful sights, and you learn a bit about the river and gorge as well. Another thing to look for, the indigenous fishermen will sell smoked salmon out of their cars under the Bridge of the Gods. It sounds sketchy, but I highly recommend buying some. Best I’ve ever had!
 

195k went over the dam yesterday, and 125k the day before that. Looks like the 10 year average peak time is usually around 6/17-6/23. I haven't tried shad fishing yet but sounds like it can be fun.

Summer Chinook looks like it is on the way up too.
Yep that’s super high for this time. Last year it peaked just before 4th of July which was late
 
Shad cakes, blacktail bucks, a sternwheeler cruise, and the Multnomah Falls to round out the trip
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