Wondering how to spend an easy, scenic weekend in Portland, Oregon? Here’s how!

Guys, I’m going to be honest, I wasn’t 100% in the right headspace to properly travel and enjoy Portland. In reality, I spent 6 full days there, but I only really did any sightseeing for 2 of them, which is why this is a weekend guide haha.

When I first got to my Airbnb after my trip to NOLA, I was just so exhausted, I stayed inside for three straight days and did nothing. I went to the grocery store once, watched all of “Atypical Season 2,” did any work I needed to do, and read The Luckiest Girl Alive from start to finish. I went out one day when the Hedgers arrived, but then the next day it was pouring rain, so we couldn’t do as anything.

Then, I had about 36 hours in Portland after I left the Hedgers in Eugene. I got into my hotel room around 3 pm on Saturday, briefly considered trying to go to Pittock Mansion, and instead got Chinese food and spent about 8 hours just relishing being online properly and catching up on work.

I basically, did a bunch of fun things the first day the Hedgers met me in Portland and the day of my flight when I didn’t leave until 11:30 pm, which, you know, amounts to a solid 48 hours of Portland travel! So here’s my little guide.

Before You Go to Portland

Why Visit

To me, Portland has always been the ultimate mecca for hipsters. I don’t know where I got this notion, but it’s always made me want to visit. I mean, this is a city that has a naked bike race, the world’s smallest park, and a vacuum museum! There’s a reason those, “Keep Portland Weird” murals are a thing.

Other odd facts I found. Not sure how true they are, but, hey, you never know!

  • Most microbreweries in the world
  • More strip clubs, movie theaters, and restaurants per capita than any other city
  • Known as the City of Roses for its, well, roses
  • You cannot pump your own gas
  • No sales tax
  • Recreational marijuana is legal *cough*
  • Kombucha is also big in Oregon, so get your gut bacteria ready.

What to Pack

In the time I was in Portland, the weather was anything from warm and sunny to cold and rainy, so you’ll want to pack according to the weather. In general, I’d pack or wear the following:

For bags, I use the Away carry-on, a daypack, and a crossbody bag.

Transportation Logistics

Getting In

If you’re flying in, you’ll most likely fly into the Portland International Airport (PDX). Apparently, it’s been voted as the best airport in the US, but I’m quite partial to Salt Lake City if only for all its tables and outlets.

When I was coming from Eugene, I took the Boltbus up to Portland, which puts you right downtown. If you’re coming from a city nearby, you may want to look into Boltbus’s locations.

How to Get Around

It’s really easy to get around with public transportation. You’ll most likely use the MAX Light Rail, the buses, and the streetcar. It really just depends on where you’re going, and what Google Maps tells you to take. I’d get the day pass for each day since it’s only $5.

Most of the downtown is relatively walkable as well. And, of course, if all else fails, you can call Lyft or Uber. I used Lyft mostly, and I really enjoyed my drivers. They all had 5-star ratings too!

Dealing with your luggage

Not sure how much you’re going to actually pack, but if you don’t want to leave your luggage with your hotel after you check out on Sunday, you could always leave it at the airport. Pass Baggage Claim Carousel 10, there’s a little baggage office. It’s $10/bag. For some reason, they don’t say that on the website?

An October Weekend in Portland

Friday Evening


If you want to be relatively central to everything, I’d stay in the Pearl District or Downtown. I stayed near the airport both times at this Airbnb and Portland Suites Airport East, so I wasn’t close to anything in particular, and it would take an hour or an expensive Lyft ride to get into town.


Grab dinner at one of the breweries around Couch Street. We grabbed a bite to eat at Von Ebert Brewing. I don’t drink, so I can’t speak to their beer (everyone else seemed satisfied with theirs), but their pretzels and tater tots were delicious.

Other breweries with high ratings include Rogue Pearl Public House, 10 Barrel Brewing, and Deschutes Brewery.


Stroll over to Voodoo Doughnut for dessert! It’s a small walk, but, hey, you’ll burn off some dinner calories before getting one of their fun doughnuts.

Visit Powell’s City of Books

You could actually do this before heading to Voodoo Doughnut or circle back depending on where you’re staying and how much you want your sugar fix. Powell’s is the biggest independently-owned bookstore in the world. I wasn’t super impressed when I saw it from the outside, but, wait until you get inside. It’s not just one floor. It’s a whole bunch of floors with books on books on books.

If you really want a treat, go to the rare books room and marvel. I could have spent hours just reading all the titles and descriptions.


Get ready, because ideally today’s a big outdoors and walking day! To the west of the Pearl District and Downtown are Washington Park and Forest Park. If you want, you can pack up your daypack with some lunch and water.

Start at the International Rose Test Garden and the Japanese Garden

If I did my time over, I’d head over to these gardens around midmorning. The rose garden opens pretty early at 7:30 am, but the Japanese garden doesn’t open until 11 am.

I never made it to either of these places (the photo is just a close-up photo of a rose I saw at Pittock Mansion, shhh). By the time I realized there were still quite a few roses hanging around in late October, I was so tired, I just wanted to get to the airport, and the Japanese Garden closes crazy early at 4 pm!

Anyway, they’re right next to each other, so they’ll make for a nice, leisurely morning.

portland in a weekend

Take in the city views from Pittock Mansion

If you wanted to, you could walk from the Japanese Garden to Pittock Mansion, and it would take you about 40 minutes, relatively uphill. Otherwise, I’d use Lyft to take you right up to the entrance since public transportation will take just as long as walking (and you’ll still be walking a good chunk of it).

I didn’t go into Pittock, but it has some cool history and exhibits if you’re interested. I was more hoping to see out to Mt. Hood from the mansion’s viewpoint. Sadly, I wasn’t able to see it since it wasn’t clear enough. It’s a bummer because earlier in my trip, we froze our bums off near Trillium Lake for two days hoping to catch the peak but no luck!

portland in a weekend

Walk the Wildwood Trail down towards the Witch’s Castle

From Pittock Mansion, I saw it was about 2 miles downhill to the Witch’s Castle, which looked like a cool, random abandoned cottage. It’s okay. The name is cooler than the actual structure, but the walk is pretty enough on its own. You never know what you’ll pass by either! I saw someone filming a movie or something, and it looked intense. All I saw was some girl in a blue wig holding the chain of another girl in a white dress and one of those face muzzles.

portland in a weekend

Late Lunch

Near the entrance to the park where the Witch’s Castle is, there are some picnic benches, so you could always eat your lunch there.

Or, if you’re like me and can’t plan ahead, you can get a Lyft and head back into town and get lunch at Little Big Burgeron NW 23rd Ave. Across the street is Blue Star Donuts, so you can compare it to Voodoo, or go to Salt & Straw for some ice cream. Apparently, you can skip the looooong line by getting a pint, but I’m not too sure as I already had a donut. I did get some Salt & Straw at the airport — the honey lavender is pretty good!

Evening Activities

After all this, it’ll probably be around 4 pm or a bit later. I’d probably head back to my hotel and get a shower or clean up. If you’re still feeling energized, there are a lot of cool things to do in the evening around Portland. The coolest is probably visiting a McMenamins Kennedy School, which I didn’t do. Stephanie, Ryan, and Kerby went, though, and they thought it was awesome.


Depending on when you leave on Sunday and if you have a car, you could do a few different things on Sunday.

Visit Multnomah Falls

If you have a car, this is a super easy Sunday morning drive. The falls are stunning, and they’re part of the Columbia River Gorge. It’s actually the tallest waterfall in Oregon at 620ft (189m).

Alternatively, you could do a half-day tour out to the falls and the gorge.

Start at the Lan Su Chinese Garden

This such a charming little garden, and it’s so beautiful. It was designed by artists and architects from Suzhou, known for its Ming Dynasty gardens, and is considered one of the best Chinese gardens outside of the country.

Wander around the Waterfront

If you don’t want to go out of the city, then I’d stay in and spend the day wandering near the waterfront. It’s just a really nice walk, especially in the fall, and you can see all the different bridges the city has built over the years.

portland in a weekend

Grab Lunch at the Portland Saturday Market

Don’t let the name fool you, it’s open on Sundays too. There are a bunch of different food stalls as well as random shopping. Grab whatever you want to eat, and enjoy the water! I didn’t get anything when I walked through, but there were seriously so many options, I was tempted.

Walk down to the World’s Smallest Park

Burn off your lunch calories by walking through the park down to the Mill Ends Park! I’m not going to lie, it’s literally just a little thing, and if you’re expecting a big “wow” moment, you’ll be heavily disappointed. However, if you just want to just see this random, quirky thing, enjoy!

Head Home

If you’re taking a Boltbus, the stand is super close to the Lan Su Chinese Garden on NW Everett St. Otherwise, you’ll want to get on the red MAX line to get to the airport. Of course, if you drove, then you already know the drill.

And there you have it! The perfect Portland weekend.I obviously am missing a TON of cool things to do around the city, but I think for a quick weekend trip, this covers quite a bit without being go-go-go.

What spots do you recommend for a weekend in Portland?

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The USA is a massive country, and I always love discovering new places to visit. I’m actually pretty sure I’ll still be hearing of new gems when I’m 90 years old and need a wheelchair to get around! Since I’ve been interested in travel, I’ve visited a number of different places in the US alone. Check out some of posts:

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Spend the perfect, easy weekend in Portland, Oregon with this itinerary! #portland #oregon #portlandweekend #thingstodoinportland

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