re: Wedding in Portland (OR) in late October

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.