• Roxii Hoare-Smith

5 Things to do in Portland, Oregon in 24 Hours

Updated: Dec 28, 2019

Keep Portland Weird…

Towards the end of our American adventure we stopped off in Portland, Oregon where we stayed for two nights. You can easily see Portland in a day (as we did) but if we had longer it would’ve been great to visit the nearby wineries. There are over 700 wineries in the state of Oregon and they are most famous for Pinot Noir as Oregon is regarded as one of the premier Pinot-producing regions in the world!!

Portland reminds me of a lot of East London with it’s street art, food trucks, quirky fashion and cafes/restaurants which specialise in just one food (such as cookie dough). Portland is such a cool and trendy city, making it the perfect place for a chilled out city break. Plus it was the cheapest placed we visited throughout the whole two months.

Here are my top Portland picks which we managed to do in just 24 hours.


Make sure you arrive in Portland hungry as there’s a lot of food to be trying. There’s a large variety of food trucks and street vendors to choose from all over the city.

There’s also A LOT of great cafes, restaurants and diners – too much food, so little time. My favourites included The Roxy diner – not just because of the name – for late night snacks and great eggnogg. We also stayed there until gone midnight just chatting to the locals, it was great fun.

For breakfast I loved Brunch Box as it was so cheap! On home game days Brunch Box have special offers on food and drink and luckily our one full day in Portland was on home game day! So I took advantage and ordered a Mimosa, Grilled cheese and Hash browns for just $8!! Also the Mimosas come in take away cups so we finished these off while shopping.

Portland first food hall, Pine Street Market, is a great place for grabbing a bite to eat as there’s something for everyone: burgers, BBQ, ramen, hot dogs, pizza and tapas as well as coffee and juices. We particularly enjoyed the $3 beer and tapas at Pollo Bravo.

Portland is known for VooDoo doughnuts – a quirky doughnut store selling unique doughnuts – think bubblegum, beer and grape flavoured doughnuts – which are served in pink boxes! I had been dying to go here for so long but we actually managed to visit the Austin store a few weeks earlier and sadly weren’t too impressed so didn’t bother going again.

I got my cookie dough fix (which I had been waiting for for 8 weeks!) at The Cooke Dough Cafe. Portland has plenty of unique cafes like this and is often where these trends begin before moving onto New York and London – and they are no where near as busy so there’s no worry about long queues or it selling out!

2. Drink ALL the beer and wine

We were in Portland for such a short amount of time that I didn’t get to try any wine (a reason to go back though right?). BUT I did drink a lot of beer which Portland is also known for – Portland has the most microbrews per capita.

Shift Drinks was my favourite place because here you can get pints for $3. THREE DOLLARS. We were amazed by this as the exchange rate was so poor for us while we were there so everything was just so expensive – it wasn’t unusual to pay $8 a pint plus tax and tip. So you can imagine my joy at finding $3 pints…

We loved The Independent Sports Bar & Grill for good beer, nachos and to watch the sports and dive bar Yam Hill Pub for good vibes and cheap drinks – and they sold cans of PBR so of course I was happy.

3. Go Shopping!!

Portland has a great variety of stores plus there’s no sales tax in Oregon so if you are planning on doing a bit of shopping on your American trip, here is the place to do it.

I bought a pair of Vans for £40 which was £20 cheaper than in the UK. There are also lots of cool and quirky independent stores and boutiques as well as Oregon stores to pick up some state souvenirs.

Visit the fashionable Pearl District for shopping (top brands as well as independent boutiques) and the famous Powell’s City of Books as well craft breweries and artisan coffee shops.

4. See the Trailblazers play

Before I went to America I wasn’t that interested in sports but this trip completely changed me. After watching games over the past few weeks I was SO excited to go to a basketball game in Portland instead of just watching it on the TV screens in a sports bar. I was so excited I even went shopping a few hours before the game to buy a Trailblazers t-shirt.

We managed to get tickets for $25 each (but you can get midweek tickets for as little as $12) and had a great view of the game where we saw the Trailblazers play the Milwaukee Bucks. I loved the whole experience: the over priced but very tasty beer and hot dogs, the cheerleaders (I felt like I was in a movie haha), and the half time and pre-game entertainment.

Tonight I went to my first ever NBA game and saw the Portland Trailblazers play the Milwaukee Bucks 🏀 The Trailblazers may have lost but I had beer and hot dogs so I’m happy 🌭🙌🏻😬 #ripcity #PDX#PDX A post shared by Roxii Hoare-Smith 🦄 (@studdedkissesblog) on Nov 30, 2017 at 10:15pm PST

5. For the Freedom

In Portland anything goes as its just so chill and that’s why it reminded me of London. Nobody looks at you twice if you go out with bright pink/purple/blue/green hair or if you want to wear bright red flares or PVC trousers (compared to other cities in the US and Europe I’ve visited!)

In some ways Portland may look like its from the 90s but its mind is definitely far into the 21st century. Portland embraces its uniqueness and everyones individual style. This is why Portland was my kind of place and one of my favourite stops on our trip.

Where to Stay

We stayed at luxurious The Benson Hotel located in downtown. This grand hotel opened in 1913 and has a classic European style lobby which is extremely striking with Austrian  crystal chandeliers, Italian marble and woodwork imported from Russia. The opulent hotel boasts many accolades including ‘Best Portland Hotel’ and ‘Most Romantic Hotel’ and is a recommended hotel by Conde Nast Johansens.

The Benson Hotel was opened by Portland lumber baron, philanthropist and visionary Simon Benson. He retired at 60 to begin a decade of public service and philanthropy. He is responsible for the 20 bronze drinking fountains around the city – he donated $10,000 to the city to have these installed.

We arrived on 29 November so The Benson Hotel was very impressively decorated for Christmas.

We visited on the day of the launch of The Benson Hotel’s Gingerbread Masterpiece by Chef Dave Diffendorfer. It was his 25th year creating the masterpiece which for Christmas 2017 featured a candy and gingerbread representation of the Lichtenstein Castle.

Chef Dave Diffendorfer has been creating his gingerbread masterpieces at the hotel for 25 years. He uses around 150 pounds of gingerbread and 20-25 pounds of white chocolate and marzipan. The masterpiece was absolutely incredible, you would not believe it was made of chocolate and gingerbread!

We enjoyed the celebrations with Christmas cookies and non-alcohol apple cider – sparkling and hot. These were potentially the best cookies I have had ever.

Upstairs a band played Christmas songs getting us into the holiday spirit. It was an amazing celebration and a great start to the season!

Our room at The Benson was so cosy with the largest and most comfortable beds I have ever slept in and was complete with fluffy faux fur throws and pillows.

The Benson offers complimentary wifi, newspapers, morning tea and coffee in the lobby. We made use of the Business Centre which was useful in printing off our boarding passes and basketball tickets.

The hotel is pet friendly, for $25 per stay dogs are provided with a Tempur-Pedic style doggie bed, a pet friendly guide and a take home gift.

The luxurious bathrooms offered Gilchrest and Soames toiletries and other necessities for a short stay such as Crest mouthwash and luxury body lotion.

As if our stay couldn’t get any cosier, our room came complete with slippers and dressing gowns. I loved the design of the dressing gowns – black with a gold embroidered Benson Hotel emblem – which had a stylish edge compared to your average hotel gowns.

As a nod to its elegant past, the hotel has an old school glamour design to it. Coast Hotels has thoughtfully restored the hotel to its original grandeur.

The Benson Hotel has a sophisticated ambience to it yet it is still a relaxed and extremely welcoming place. The Benson Hotel is an iconic Portland landmark and is known throughout the States as one of the country’s grandest hotels. Every U.S. president since William H.Taft has stayed n the hotel.

Our room offered great views of SW Broadway including the US National Bank building.

How to get there

We travelled to Portland by train from Seattle (Amtrak Cascades) which took around four hours and cost $26 one way. We enjoyed great views of the Washington countryside and also went through areas where Twilight was filmed.

Getting Around

Portland is very walkable so we didn’t use public transport or taxis the whole time we were here – except to get the airport which is around a 30 minute drive. We ordered an Uber to take us to the airport and a karaoke uber picked us up! The uber had a live YouTube show every Friday and Saturday. The car was complete with microphones, strobe lighting and a basket full of candy – if only ever taxi was that fun!?

 The Amtrak station is a short walk to downtown so is also very easy to get to.

Portland is a great city to just wander around admiring the street art and the quirky stores whilst enjoying the beautiful aromas from the food trucks.

You can also get around the city by hiring a Biketown bike – these are based all around the city. The city puts bikes firsts and has wide bike lanes and ‘bike boxes’ at intersections. 

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