Best areas in downtown Portland OR

My wife and I are planning a 3-4 day trip in mid-May. Which areas are best for walkability and which are safer?

We’ll probably rent a car as I’ve convinced her to do one day of wine activities in Willamette (However, if we only need a car for one day, we may find an alternative to doing a rental for the entire time).

Just don’t plan on going to Wal-Mart. I stayed in a hotel built atop Macy’s, which is kind of a neat idea. It is on the main square downtown. Easy walks to restaurants and a few wine stores. I’ve also stayed at hotels a couple blocks away. Names escape me. Plenty of homeless in downtown and they all have big dogs. Wonder how they can afford to feed the dogs. Driving downtown is a hassle with cars and light rail fighting for space. Try to avoid cars until you go to wine country.

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Recently stayed at the Kimpton and I would recommend it.

Cheers

Inn at Northrup Station is in a walkable area and on the street car. It’s near NW 23rd Ave that has restaurants, bars, shops. If you wanted a night in, the rooms have a kitchen. Plenty of grocery in the area. New Seasons and Zupans Market are worth the trip even if it’s just to browse (wine or food). Vinopolis and Liner & Elsen (do Friday and Saturday tastings) wine shops are close too.
Tents are under bridges in this area.
In the area I recommend G-Love, Mama Bird, St Jack, Phuket Cafe/LangBaan LangBaan is a tasting menu done on weekends. Hard reservation to get- have to plan ahead. West is supposed to be good too. Plenty of great pizza and Italian in the area. Just a Pasta or Fillmore Trattoria are solid choices. Many places on NW 21st too.
Great French bakery is St Honore.

I’d agree with Stephen on a lot of his recommendations for NW. I work in that area and there’s a lot of variety around there. You could also try staying at the Hampton Inn and Suites on NW 9th and Everett. I’ve never stayed there but it’s also near a number of restaurants and bars.

I don’t find driving in Portland any worse than any other bigger city, but I do it every day, but there’s far less traffic than SF or LA.

If you have time for dinner let me know and we could meet somewhere near where you are staying. There are a few places in town that will still let me in the door.

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The MAX Red Line goes from the airport to downtown Portland. It continues on to Beaverton and you can pick up a rental car there from Enterprise to visit Willamette.

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Pre-pandemic I travelled to Portland regularly and have stayed in a bunch of different hotels around downtown. My preferred area is what I consider northeast downtown near Powell’s Books and Whole Foods. Powell’s is a must-visit for me and who wants to lug 25 pounds of books 20 blocks to get back to your hotel. Whole Foods was a common stop to pick up food/water, etc. to bring back to the room. I also like the area between Powell’s/Whole Foods and the Pearl District better than the rest of downtown for restaurants and shops.

Generally I found that the sketchiness factor seemed to increase the closer to the river one gets but it is all relative in Portland.

Agree with others about the usefulness of light rail to/from the airport. I personally wouldn’t keep the rental car for more than the Willamette trip. The few other places (restaurants) you might want to go are near enough downtown that Uber/Lyft would be much cheaper.

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Nice to see the James Beard Public Market is moving forward and looks to open sometime in 2026. I’m generally not enthused by food halls or markets with a big name behind them but this area of downtown PDX was really hurt following the riots in 2020 and there was warranted talk of it going the way of Detroit so this is a very welcomed opening in a spot that sat vacant for a long time.