Portland Weekend | The Best 2 Day Or 48 Hour Guide For Portland Oregon

Portland, Oregon

Are you planning a Portland weekend trip? Or do you just have 2 days or under 48 hours in the City of Roses? A few years ago I spent 4 months in Portland while I was spending time with local friends and doing freelance work at Nike. If you go through my guide, I do have a lot of Portland and Oregon content that may be helpful for your planning. Even though I have not been back in a few years, I asked some of my local friends with good taste for some updates. They shared a handful of new places to stay, eat and drink at if you’re planning a Portland weekend. 



Portland Weekend Guide



Getting In 

By Plane

When flying into Portland, you will be arriving at Portland International Airport. You can take public transit called “Max” from the airport to downtown. The ride on the Max is about 38 minutes. Tickets are $2.50 one way for an adult. You will find ticket machines and the station on the lower level of PDX airport. 

From the airport, a taxi cost about $35. Radio Cab is the local taxi company and first-time users can get a discount on the website or app. The drive is about 20-40 minutes. 

By Train 

If you are coming into Portland by train, you will be coming by Amtrak and they arrive and depart at Union Station. 

By Bus 

Greyhound and Bolt Bus service the Portland area. Greyhound is the biggest bus company in America and goes all over the country. Bolt Bus is another bus company but only serves the Northwest corridor. They go to Vancouver, Seattle, Bellingham or south to Eugene and Albany.

**Disclaimer: This post may contain affiliate links. There is no additional cost to you, if you click through an affiliate link and make a purchase, I may make a commission.**

Getting Around

Portland is pretty easy to get around. You can get around by car, bus, bicycle, Max light rail, streetcar, or walking. Driving is easy if you’re coming by car or renting a car. Parking is not too bad either. Busy areas have parking metres that accept coins or cards but you can often find street parking (depending on the neighbourhood). Be mindful of things in your car though. My car was broken into and everything inside was stolen. If you need a car, car sharing services ZipCar and Car2Go both operate in the city. 

There is now a bike-share service in Portland called BikeTown. If you are walking around, you can also supplement your explorations with Uber and Lyft ride sharing. 

Where To Stay

Over the years I have stayed at a handful of hotels in Portland. My last hotel stay was at the Kimpton Hotel Monaco but I have also stayed Hotel Lucia and Hotel Deluxe a long time ago. While I haven’t stayed at the AC Hotel By Marriott Portland, I have stayed in a handful while travelling through Europe and love their minimal design vibe. Of course, there’s the Ace Hotel or the Nines, A Luxury Collection Hotel

Read more: A Detailed Review Of The Kimpton


Hotel Monaco Portland

Enjoying robe life at the Kimpton in Portland

New hotel openings in Portland include Porter and Canopy by Hilton, Jupiter Next, Hi-Lo, and the Hoxton

Air Bnb

If I am not staying in a hotel, I stay with local friends. So I can’t recommend a specific Air Bnb but they do have a lot of listings in Portland. If you haven’t used Air Bnb before, use my link to get up to $40 off your first stay. 

When I have stayed with friends in Portland, my favourite neighbourhoods are the Southeast and Northeast. In the Northeast, around Alberta and in the Southeast, near Division or Hawthorne. 




  • Flights: Find a cheap flight using Skyscanner or Momondo. I like these two booking sites because they both search all websites and airlines around the globe including budget airlines.
  • Accommodations: I use Booking.com or Tripadvisor to find the best rates on hotels. Hotels.com offers a free night after booking 10 nights.
  • Get up to $40 off your first Air Bnb stay by using this code!
  • Travel Insurance: Having gotten sick on my travels in the past, I never travel without being insured. You never know when something may happen. For my round the world trip and extended long-term travel, I use World Nomads. For other trips, I have used Roam Right and they cover activities like extreme sports.

Look at the best Portland weekend hotel rates with cancellation on Booking.com:



Portland, Oregon

Portland Weekend Itinerary 

Portland Weekend  – Day 1 


There are so many amazing morning food options in Portland. The most important question is how long are you willing to wait. On weekends, the wait times can be quite long almost everywhere. If you really want to have brunch in Portland without a long line, go around 8 am or after 2 pm.

Trinket Breakfast

Breakfast tacos at Trinket

Read more here: Where To Eat In Portland

If you are in Portland for 2 days during the week, you have your pick of restaurants for breakfast as most places are not as busy. My recommendations would be Screen Door, Jam, and Trinket. One of my favourite parts about breakfast and brunch in Portland is the great local coffee they serve.

Portland Farmers Market 

If you’ve read a bit of my blog, you know I love going to farmers markets. When I stayed in Portland, I frequented the market on Saturdays for fruits, vegetables, and delicious treats from local vendors. Click here for more info.

Portland Farmers Market

So many tasty treats at the Portland Farmers Market 


Get Outside And Hike Or Seek A Local Waterfall

One of the best parts about Portland is the great local hikes. If you have a car, you can head east along the Columbia River to see Multnomah Falls or Triple Falls. Another hike I did was to Angels Rest. Oneonta Gorge is one popular place I didn’t visit but it is on my list for next time. 

Multnomah Falls

The stunning Multnomah Falls

Travel Fitness - hiking Angels Rest Oregon

A mandatory Portland weekend selfie

Coffee Break 

It might be time for you to take a coffee break and you’re in the best hands because Portland has amazing local roasters and coffee shops in all its different neighbourhoods. Some of my favourite Portland coffee shops are Heart Roasters, Stumptown, and Coava. But this is Portland so of course, there are new cafes opening up all the time. Now I’m keen to check out the Australian chain Proud Mary on my next visit. 

Read more here: Portland Coffee Guide

Stumptown Belmont - Portland Coffee


Need A Sweet Treat Instead?

If you need a sugar boost in the late afternoon, go to my favourite donut place Blue Star Donuts. While Voodoo Donut is very popular, it’s not worth waiting in the line. Many years ago I happen to walk by when there wasn’t a line and I tried a handful of donuts. In my opinion, they were very overrated. Blue Star makes the best donuts in Portland, hands down. 

Blue Star Donuts

The best PDX donuts

If cold treats are your thing, Salt and Straw Ice Cream is a must. They have expanded south to LA and San Diego so I’m quite thrilled. Can’t do lines but in a group? Decide on a flavour and buy a pint to bypass the line!

Try Ruby Jewel for their delicious ice cream sandwiches. When I was in Palm Springs, I found them in a local grocery store and I’ve been a fan ever since. Now they have a shop on SW 12th Avenue.

Salt and Straw Ice Cream


Time For A Drink? 

Portland has some of the best breweries in the country. You can do your own self-guided tour or you can join on an organized brewery tour. When my friends came through town we did our own self-guided distillery tour. Vegan? There are vegan bars like The Bye And Bye or Modern Times Brewery. 

Evergreen Escapes Beer Tour

Check out these Portland tours operated by Viator



Hungry For Dinner? 

Portland is one of my favourite American cities to dine in. Whatever you are in the mood for, there are loads of options. High-end, prix fixe, farm to table, food cart, budget-friendly, the city has it all.

You can dine at the popular John Gorman restaurants Tasty n Alder, Tasty n Daughters, or newish Spanish inspired Toro Bravo. In the mood for pizza? For Neopolitan style, go to Ken's Artisan Pizza. Another popular place I would order from is Hot Lips. Want tasty Asian food? Try popular Thai restaurant by Andy Ricker, Pok Pok or Paadee and Hat Yai. 

Read more: Portland Food Guide

Pok Pok Portland food

Dinner at Pok Pok

Tasty n Alder

Tasty N Alder

Offbeat Choice - Strip Bar 

Portland is notorious for its strip clubs. The reason they are famous is their wide variety of strip clubs as well as having full nudity and being able to drink liquor (If you're foreign and reading this, there are some states that don't allow a mixture of the two. Yes, I know weird.) Vegan? No problem. Like short girls? They got you covered. Prefer heavy metal? Yes, sir. Going to the peeler bar is not everyone's cup of tea but perhaps it might be yours.

As a solo traveller, it is not something I would choose to do by myself. But when I was in Portland for an extended stay, I visited a few with my local friends. Casa Diablo (vegan) and Sassy's (dive bar style) were the two I went to.  

Portland Weekend - Day 2 

Breakfast - Food Cart 

Short on time for breakfast? Try a breakfast food cart? Fried Egg, I'm In Love is a local favourite and located in Pioneer Courthouse Square. 

Fried Egg I'm In Love

Photo credit: Fried Egg I'm In  Love

Washington Park 

One of the bests things about Portland is the green space. Visit the city's most popular park, Washington Park. The rose garden in the spring is spectacular or you can visit the children's museum, play tennis, or hike the many trails. 

Portland Rose Garden

International Rose Test Garden in Washington Park 

Also located within Portland's Washington Park is the Japanese Garden. It is a wonderful Zen sanctuary in the middle of the city. Have tea and snacks at the teahouse and check out the views of Mount Hood. For more information and tickets, click here.

Japanese Garden Portland

Photo courtesy of Flickr

Pittock Mansion

Pittock Mansion was built in 1909 as a private home for newspaper publisher Henry Pittock. Now the house is a museum. The house has been kept as is and very beautiful inside as well as the grounds. If you want an excellent view of Portland, you can go behind the mansion without charge. There is a gate that closes at night, but you can catch a beautiful sunset here and even see Mount Hood in the distance.

Pittock Mansion

Pittock Mansion 


Some of my favourite places for chill vibes lunch would be Nongs for Asian, Lardo for sandwiches, and Por Que No for Mexican. 

Read more: Portland Food Guide


A delicious sandwich at Lardo 

Nong's Khao Man Gai

Nong's Khao Man Gai

Tax-Free Shopping 

The best thing about shopping in Portland is that it is still tax-free. Try visiting different neighbourhoods for shopping. The Hawthorne district has vintage shops, over by the Pioneer Courthouse are your big box stores like Nordstroms and Apple. In the West End district, you'll find local brands like Poler or Danner. 

Danner Boots Portland

Danner Shop. Photo courtesy of Danner Boots


If you're a book lover, a visit to Powells is a must. With the invention of Amazon and online shopping, actual bookshops are a thing of the past. Flipping through pages of books is something I don't do as much but still enjoy doing. Powells City of Books in Portland's Pearl District is the biggest new and used bookstore in the United States. 

Powells Books

Photo courtesy: Flickr


Some new recommendations from my local friends: Try out La Neta at the Hoxton Hotel for Mexican inspired food or street tacos at their taqueria Tope on the roof. There's a new indoor food market called Pine Street Market with some of the city's best serving up food in a more casual atmosphere. Try Pollos Bravo by Toro Bravo (from the Tasty n Alder/Tasty n Daughters family).

La Neta Hoxton

La Neta inside the Hoxton Hotel. Photo credit: PDX Monthly


Ready for some farewell cocktails? There are loads of places for great drinks. Love whiskey? Have an Old Fashioned at the Multnomah Whiskey Library. A new cocktail favourite is Hey Love inside the newish Jupiter Next Hotel

Hey Love Cocktail

Cocktail at Hey Love inside Jupiter Next. Photo credit: Hey Love

 And that is what I would do with 2 days in Portland, my friends! Have any recommendations for a Portland weekend? Leave them in the comments. 



**Disclaimer: This post may contain affiliate links. There is no additional cost to you, if you click through an affiliate link and make a purchase, I may make a commission.**

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