Wedding in Portland (OR) in late October

Portland has amazing wine country nearby in several directions.

If you are wine people, or have never spent time at vineyards, I’d recommend that.

You can be in Willamette Valley in like 35-40 minutes tops

Plenty of options to choose your own adventure with 3-4 days to play with.

The Oregon coast down to Yachats and beyond is really worth a day or more. You can pretty much just drive and hit the scenic overlooks or random beaches to check it out.

Crater Lake is pretty spectacular, especially if you can book a room in the lodge overlooking the lake. It's a bit out of the way but very impactful to visit.

Mt Hood is great. We didn't do much there but spent a night in the Timberline Lodge. (One of the real hotels used for outside footage in The Shining)

The Columbia River Gorge is spectacular with several waterfalls and we did a dam tour that was fun. It was also right next to the Bonneville Fish Hatchery for a cool 45 minute walk-about with tons of sturgeon.

The Japanese Garden is beautiful if you like that sort of thing. A few cool views that overlook the city.

The city itself I find such a bummer. It is a beautiful city with a great climate and cool things all around, but the homeless and drug problem is just a real shame. I've been through there twice for vacations. Last year we were going to just hop down at Ken's Artisian Bakery for some treats on our way out of town and every corner was dripping with fentanyl zombies and really felt too unsafe to even pop out for croissants.

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The city itself I find such a bummer. It is a beautiful city with a great climate and cool things all around, but the homeless and drug problem is just a real shame.

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Basically the same thing in SF

I was stunned when I was in SF a year ago. Just total shithole that had descended into disgusting, junkie, crime ridden filth. I was unreal.

Get right out the city and its beautiful

Stayed at The Allison in Newburg years back. One of the best trips I’ve ever taken. Keep in mind I was drunk for the entire time. I’ll have to think of some restaurants. I remember The Painted Lady was amazing.

A couple years ago, I stayed at the Howard Johnson up near the airport.

I saw some shite. 0/10

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I figured this would get political but thanks for the help everyone. Will minimize the time spent in Portland

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Even if you remove the political stuff, the best parts of Oregon are outside of the cities and out in nature. You can do most city stuff anywhere, but that part of the country has some really unique and amazing outdoor scenery and charm. Waterfalls, gorges, mountains, deserts, wine regions, an amazing coastline and some of the best state parks anywhere.

People would give you the same advice for Salt Lake City and that's one of the more orderly and conservative cities in the whole country.

Of course not everybody likes the great outdoors.