When to go to / What to do in Portland, OR

June through September is the best time for Oregon.

Portland depends on your interests. One thing I would recommend is taking a drive to the coast. Cannon Beach is a straight shot west from Portland and if you halfway like outdoors stuff and beautiful scenery, you'll love it.

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but I figure that is an awful time to go because of the cold.

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Portland really isn't cold but is gray during the winter

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Portland really isn't cold but is gray during the winter

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And sometimes the mountains won't come out to play.

A good time to come would be during the Oregon Brewer's festival - I think it is the last weekend in July.

If going to the coast, go to Cannon Beach and drive south. You'll see spectacular views. Also pencil in driving west on I-84 to Hood River and The Dalles, if you have time. If you windsurf or want to learn to windsurf, then that is the place to go. Hood river is a neat little town that is very walkable and has terrific views of the Columbia River Gorge. You can also go up to Mt Hood, and I recommend having lunch/dinner at Timberline Lodge. Yes, you can ski in the summer if you want to.

The Dalles is interesting, because it is really in the high planes and not the Willamette Valley, so the terrain is much different. Much more rocky and less green.

You can do a BNB, but sometimes you can find some terrific hotel deals if you go to Hotwire.com and reserve a hotel room in the "Pioneer Courthouse Square" area. All hotels in that section will be within easy access of The Pearl District, Pioneer Square, and Downtown Portland. Later in the summer, deal kind of dry up, though. I know a couple of people on here have found great deals.

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I went to portland and cannon beach in february and still had a great time.

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Summertime is definitely the time to be in Portland. Places like Great Notion open up their outdoor spaces and it makes it feel less packed. Portland is extremely walkable in the summer, and less so in the winter - especially for you southerners who aren't used to the dreary winter weather...

Just skimming this thread because I’ll be in PDX next month and realized that I will be there for the brewers fest weekend. Is there Anything new or up and coming on this list that I wouldn’t have had there a couple years ago when I visited?
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Also visitng bend for a couple days so if I will Be able to get it there I won’t need to drink it at the fest and can drink on the other stuff

Great Notion won't be available in Bend. A lot of the beers at the Brewer's Fest will be one offs, so until they release the actual beer list, you won't know.

Crux Fermentation Project is the place to be at the end of the day in Bend. Their outdoor space is amazing. I usually float down the Deschutes in the middle of town when I'm in Bend. An innertube, a couple of beers, and the sunny weather make for a very relaxing day.

Don't forget that the local breweries may not be busy during the festival, which is a good thing.

Many breweries probably don't know what beer they'll be entering. That's a good thing, IMO, because it probably means some one offs. Sounds like you've been, before.

You probably know that the festival is mainly summer beers because it's July. Yeah, get their early to avoid the crowds, and it's just about perfect.

For 27 year-olds, I would recommend that you stay in the Pearl District, Pioneer Square, or Buckman Districts. Especially if you are looking for a hotel. Closer to the river (within 5-15 blocks away is best) is better and closer to Burnside St is better. I say this because that will give you the more things to do without a car. That comes at a price, although I've seen nice hotels under $100/night right by the river. July and August are probably the most difficult times to find bargains, though. Depending on how much Ubering you plan on doing, it may be worth the extra $$. If you rent a car, plan on paying for parking in this area. Honestly, if you stay here, you won't need a car, because so much is within walking distance and the train will take you right here from the airport if you're flying in.

Northeast Portland on Alberta street or Mississippi Avenue is cool. Southeast Portland on Division or Hawthorne is also a fun area, but you'll have to drive or Uber to see a lot of the city.

The west side is the "downtown" area, and there is more to do in a walkable area. It is also newer, nicer, and more expensive.

The east side is a little more spread out, especially as you get further from the river. The east side has more quirky neighborhoods and is where the hipsters live. When I say quirky neighborhoods, I mean bar/restaurants/shops, etc. There are things to do in those neighorhoods, but you will want to branch out from there.

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Yeah you helped me plan my whole trip last summer!

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I remember that, but I didn't remember that you went to the Oregon Brewers Fest. That festival is a lot of fun, to just soak up the atmosphere with the mountain and the river right there.

I enjoy those neighborhoods on the east side with all those craftsman homes, mature trees and bar/restaurant districts. Very authentic and shows that Portland was a well designed city going back 100 years.

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Thank you for the recommendations. Really appreciate it. I've been reading and would anyone suggest staying in Cannon Beach? It looks like the first thing everyone on here suggests is driving down there.

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I've stayed in Cannon Beach 3 times and loved it. I go to enjoy the outdoors, and Cannon Beach is in a good place for that. Ecola State Park is just north, Oswald West State Park is just south and both are very nice. The entire coast south of there has multiple beaches/points to enjoy and Haystack Rock is basically in Cannon Beach.

If you want more of a city time, it isn't that. I've gone to be laid back and wander around the beach and outdoors. Cannon Beach is excellent for that. We've stayed at the Wayside Inn all 3 times and it is a reasonable price a tiny park away from the beach.