A Weekend in Portland, Oregon

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Portland is Oregons largest city situated in the north of the State on the Willamette River. It has a famous slogan “Keep Portland Weird” and it is weird but in the best way! A weekend in Portland is the perfect city break, it has a lot to offer for visitors from craft beer and street food to bookshops and roses – this city has something for everyone.

Here’s our guide on what you should not miss when planning a weekend in Portland, Oregon.

Downtown Portland

How to get to Portland Oregon

Portlands airport is well connected to most other cities within the US as well as some international locations. Portland International Airport – PDX – is located just on the outskirts of the city and public transport can have you in downtown Portland within 45 minutes. Uber or a taxi will take about half an hour.

Amtrak Train
Train from Everett Washington to Portland Oregon

Portland also has a central train station which connects to cities along the West Coast of the USA as well as the Mid Western cities such as Chicago and Minneapolis–Saint Paul. Portland Union Station is right in the city centre and if your hotel is located in the centre you can most likely walk there from the station. Union Station is also where the train from PDX terminates.

Where to Stay in Portland

There are two hotels we recommend in Portland, both are McMenamins properties. Choose whether you want a city centre location or to stay in one of Portlands popular neighbourhoods. Neither is a disadvantage as you will be exploring the neighbourhoods as well as the city centre.

McMenamins Crystal Hotel

The Crystal Hotel is located in downtown Portland, right in the middle of all the action. You will be in walking distance from many of Portlands must see attractions. It is also ideal if you plan on seeing a band play at the Crystal Ballroom nearby – also a McMenamins property.

McMenamins Kennedy School

Stay somewhere really unique. Possibly our favourite hotel in Oregon is the Kennedy School. McMenamins have converted this old school into a quirky hotel complete with several bars, restaurant, cinema and pool. Of our two recommendations this one is the more family friendly of the two if you’re travelling with children. If you’re travelling as a couple you can’t go wrong with either the Kennedy School or the Crystal Hotel.

Day 1

Your first day of a weekend city break is generally taken up by travel. You may arrive in Portland for a late lunch but most likely will arrive in time to check into your hotel mid-afternoon. However no matter what time you arrive in Portland on your first day there will be something to do.

City Centre Attractions

One of our favourite places to spend time in Portland is Powell’s City of Books. Powell’s is the largest independent book store in the world and it takes up an entire city block. Inside there are over a million of new and used books to browse or buy as well as a few souvenirs and a cafe for refreshments. You could spend hours inside this store so you might want to set yourself a time limit before going in!

Spend sometime exploring the walkway along the Willamette River. It’s a great place for photography and if you’re in Portland during the Rose Festival you will find all sorts of things going on in this area. Navy ships, dragon boat racing, fair rides and craft stalls.

Depending on which day you’re arriving if it’s a Saturday then check out Portland’s Saturday Market near the Willamette River. It’s made up of craft stalls and street food. Expect to spend around an hour or so exploring the Saturday Market, it’s not huge but there’s enough to make it worth having a look around.

Food Recommendation

For your first meal of your weekend in Portland make sure you head to one of the food trucks. Portland is famous for its variety and quality of street food. We love the 5th Avenue Food Cart Pod, we’ve tried a few of the food trucks there and they’ve all been great. Grilled Cheese Grill is one of our favourites. If you’re a fan of Grilled Cheeses – who isn’t? then give it a try!

5th Avenue Food Cart Pod, Portland

Another must stop for food for us while in Portland is Voodoo Doughnuts. The vibe they have can only be from Portland, you won’t find these doughnuts anywhere else and they taste great too. Grab yourself a pink box at the start of your weekend in Portland to work your way through a few varieties while you’re there.

Where to have your first drinks

There are loads of bars in Portland specialising in everything from craft beers to whiskey. Try a range of bars while you’re in town, we recommend you try one of the McMenamins bars – a no brainer if you’re staying there. Also do not miss the Multnomah Whiskey Library which has a collection of over 1000 whiskeys plus 600 other spirits to choose from. You are allocated your own bar tender in the Multnomah Whiskey Library to help navigate the extensive menu!

Multnomah Whiskey Library, Portland

Day 2

Portland is surrounded by natural attractions, Oregon is an outdoor enthusiast paradise. On your full day in Portland we’re going to recommend something we wouldn’t normally recommend for a city break – get out of the city.

If you haven’t visited the Saturday Market already you might want to do that first today. Afterwards collect a car from one of the many rental car garages in the city centre and head east out of Portland to the Columbia River Gorge.

Columbia River Gorge

Columbia River Gorge from Vista House

Join the Historic Columbia River Highway at Troutdale on the outskirts of Portland. Plan to drive this Historic Highway all the way to Dodson and consider driving further to Cascade Locks before heading back into Portland.

The Historic Columbia River Highway has some of the best waterfalls and panoramic views in Oregon. Plan to spend a few hours on this route with most of your time being spent outside of the car on short hikes to waterfalls. Even those who don’t hike can enjoy it as some waterfalls can be seen right from the road so it’s a suitable activity for pretty much everyone.

You will rejoin the main highway at Dodson but keep heading east to Cascade Locks, it’s not far. While in Cascade Locks take a look at the Bridge of the Gods. You can walk across the bridge if you have the time for some more spectacular views of the Columbia River Gorge.

We can recommend Thunder Island Brewing in Cascade Locks as your lunch stop. You can sit outside on the rivers edge which is beautiful. You can park for free here and it’s a good point to turn back to Portland if you’re just out of the city for a few hours.

Portlands Neighbourhoods

While you still have the car explore some of Portlands neighbourhoods.

Alberta Arts District

The Alberta Arts District is a vibrant area of art galleries, restaurants, clothing boutiques and gift shops. Our favourite ice cream shop is on Alberta – Salt & Straw, you won’t find flavours like these anywhere else. There are also a good range of bars on Alberta, you might want to allocate a designated driver until you return the car.

Pearl District

Head back into the city centre and return your car. Pearl District is the area to the north of the city centre. You may have seen some of this area on your first day in Portland as Powell’s City of Books is on the southern edge of Pearl District.

Pearl District is full of independent shops and craft brewery bars. If you want to do some shopping during your weekend in Portland then this is the place to come to. When you do want a break from shopping and if you don’t want to visit more of the bars then you will also find plenty of coffee shops in Pearl District too.

Day 3

On the morning of your last day of your weekend in Portland head to another neighbourhood in time for breakfast – Sunnyside.


Sunnyside has a bit of everything Portland is known for within a few blocks with many locally owned coffee shops and restaurants. For breakfast we recommend you head to Slappy Cakes where you can make your own pancakes. A great place for adults and kids a like.

You might find there’s a wait to get into Slappy Cakes – it is very popular. If you do have to wait we can recommend a great independent coffee shop nearby. Never Coffee across the street makes a great cup of coffee, by the time you have finished your drink here your table at Slappy Cakes should be ready.

You might want a walk after breakfast at Slappy Cakes. You have a couple of options, either head south onto Hawthorne Boulevard to explore even more independent shops and cafes or head north and walk through Laurelhurst Park.


Whichever option you chose, Hawthorne or Laurelhurst, after breakfast head back into downtown Portland through Buckman. It will take you around an hour to walk back into the city but it’s through another of Portlands hip neighbourhoods.

Buckman has the huge range of independent coffee shops and bars you will have now come to expect when walking around Portland. There are also plenty of shops in this area too. We recommend you walk through Buckman aiming to get towards Burnside Street on the northern edge of Buckman before crossing over the Willamette River back into downtown Portland. This is because if you cross the Burnside bridge over the Willamette River you can get the iconic picture of Portlands white stag sign before you return home.

We hope you find this guide for a weekend in Portland useful. Let us know what your favourite sights (or breweries!) are in Portland in the comments!

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