Welcome to Portlandia: a weekend in Portland, Oregon

Welcome to Portlandia - LiveRecklessly

A clown sporting tartan overalls and a bold blue afro stands on the sidewalk, accompanied by two friends dressed like GWAR bandmates.

It sounds like the opener of a very weird joke. But it isn’t. It’s just Portland.

It was October 2015. Myself and four fellow Aussie expats had piled into the car in the early hours of Saturday morning to make the ferry ride and road trip for a weekend in Portland.

As we drove down Washington’s coast, we joked that the person who saw the weirdest or most hipster thing on the trip would win a prize. Who knew that this would be achieved within seconds of entering the city limits?

Beyond the hipster stereotypes and notions of the city as a sanctuary “where young people go to retire”, Portland revealed itself to be a hardworking, unique city. One which in the face of economic recession and high unemployment, cultivated a community spirit of entrepreneurship and creativity.

Welcome to Portlandia: A weekend in Portland - LiveRecklessly

Welcome to Portlandia: A weekend in Portland - LiveRecklessly.com

I returned for another weekend in Portland in May this year. Both trips have instilled in me the importance of supporting local business.  It seems to be this culture that enabled Portland to build itself as a major player in American food, arts and culture.

While it’s easy to make jokes about the plaid shirts, lumberjack beards and fixie bikes, how many other cities can boast more than 80 craft breweries in the metropolitan area? In how many cities do independent clothing boutiques truly outnumber big box chains? Or where the most renowned restaurants source produce from only local purveyors?

I think there is a lot to be learned from Portland.

Welcome to Portlandia: A weekend in Portland - LiveRecklessly.com

Welcome to Portlandia: A weekend in Portland - LiveRecklessly.com

While much of my time in Portland has been spent devouring the city’s best food and drink, my satisfied stomach took small breaks to wander in search of sights and attractions.

Here are some recommendations for what to do on a weekend in Portland.

Free Walking Tour

Hands down, the best thing you can do in Portland.  If you’re short of time in Stumptown but still want to get a good feel for the city, I highly recommend taking a free walking tour with Secrets of Portlandia. I took this tour on my first visit, and was so impressed I signed my sister up when we came back in May.

Our guide Erik was incredibly knowledgeable about his city’s history. From its origins on the Oregon Trail, to the social and political impact of the recession, to the food cart revolution and beer obsession. To being one of the world’s first cities to develop environmental policies to reduce the carbon footprint of every resident and combat climate change.

The tour was extremely informative, but it was Eric’s enthusiasm, sense of humor and passion for his city that really came across. The humble beginnings of this now hugely popular daily tour were formed when Erik himself could not find employment – so he started the tour! As experienced by many of his peers, job opportunities were rare and as a result many people started their own businesses.

Tours run daily at 11am, starting at Pioneer Square. Tip your guide nicely!

Welcome to Portlandia: A weekend in Portland - LiveRecklessly.com

Welcome to Portlandia: A weekend in Portland - LiveRecklessly.com

Portland Saturday Market

Portland’s largest outdoor arts and crafts market is a must do. It showcases 350 Pacific Northwest artisans, and offers everything from clothing to food to jewellery and pet accessories. There’s no doubt you’ll leave with something interesting for your souvenir collection – and it’s a great way to support local artists and small business.

Despite its name, the market is open both days of the weekend, from March through to December.

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Powell’s Books

Any bibliophile will be impressed by Powell’s, the world’s largest independent new and used bookstore. It’s so huge there are even store maps to help guide visitors. Throwing caution to the wind, I went map-less and came away with five new additions for my bookshelf.

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Lan Su Chinese Garden

Located in Old Town Chinatown, the Lan Su Chinese Garden is the quiet escape you may want on a city weekender. Taking up an entire city block of space, you’re free to explore in peace – but I highly recommend finishing your visit with tea by the Tower of Cosmic Reflections.

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Portland Art Museum

Portland Art Museum is actually the oldest art museum on the west coast. While the $20 admission is a little steep, it’s easy to spend hours here exploring even just the permanent collection (tip: the first Thursday of every month is free admission 5-8pm).

My favourite was the Impressionism exhibit that featured works by Van Gogh, Monet, Renoir and Robinson. However, the museum has an extensive collection of Asian, European and Native American art to enjoy. I even found something for the cat lovers…

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

If you’d rather spend your time outdoors, there’s still plenty of art to be found on Portland’s streets.

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

International Rose Test Garden

Portland is also known as the City of Roses, so it pays to head straight to the source: the famous International Rose Test Garden. It’s the oldest rose garden in the USA.  Fun fact: it started as a haven for European experimental roses during the First World War.

Our May visit coincided with the Rose Festival, when each garden was bursting with full blooms of colour. I loved wandering through the Shakespeare Garden the most. It really is worth a visit – both to see thousands of roses and take in the lovely Portland skyline view below the park.

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Where we stayed on our weekend in Portland: Hotel Vintage Portland

While I tend to book most of my accommodation via Airbnb, there is still one exception – boutique design hotels.

Hotel Vintage by Kimpton was an epic hotel choice for our stay. The entire place looks like an art gallery… or perhaps Anna Wintour’s house.

There’s the daily hosted wine hour with complimentary tastings of Willamette wines.  The epic games room with pool, shuffleboard and giant Jenga. The rooms were well appointed, beautifully designed, and home to the funkiest hooded bathrobes I have ever seen. And the downtown location made everything totally walkable. We never used our car once we valeted!

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

Welcome to Portlandia: how to spend a weekend in Portland. Read more www.liverecklessly.com

I look forward to returning for another weekend in Portland soon. Next time I’ll check out a few more breweries, tour Distillery Row, and explore more of the city’s neighbourhoods.

How would you spend a weekend in Portland?

Interested in where to eat and drink in Portland? My suggestions are coming soon!

Planning a weekend in Portland, Oregon? Experience the best of the city's culture and creativity with these walking tours, gardens, markets and museums. Welcome to Portlandia. Read more at www.liverecklessly.com Planning a weekend in Portland, Oregon? Experience the best of the city's culture and creativity with these walking tours, gardens, markets and museums. Welcome to Portlandia. Read more at www.liverecklessly.com

Weekend in Portland Weekend in Portland Weekend in Portland

19 Comment

  1. I LOVE Portland! That hotel looks so chic and quirky! Did you ever make it to voodoo donuts, blue star donuts, or salt & straw ice cream?! BEST treats in the area!

    1. I love Salt & Straw – they’ve even opened the Wiz Bang Bar at Pine St Market that sells soft serve and sundaes. So yummy! I’ve never been keen enough to brave the long lines at Voodoo, though it does sound fun. Totally recommend Pip’s Doughnuts if you’re in Portland – the chai flavour is amazing!

  2. So glad to read this! My good friend was there 2 weekend ago visiti f and was telling me all this. Yall make me want to visit 1 day! 🙂

    1. You totally should! Portland is also a great jump off point to explore the Willamette wine region or check out Multnomah Falls. I’m putting the finishing touches on a Portland Food article so come back to check that out too! Always happy to offer suggestions when you book your visit 🙂

  3. Sounds amazing! I want to visit the states, will definitely need to add Portland on to the itinerary! Thanks for the tips!

    1. I totally recommend it 🙂 So many international visitors stick to the LA/San Francisco/Vegas/NYC route (I pretty much did on my first visit!) – but I think the best of the US can be found elsewhere, particularly in the Pacific Northwest!

  4. The photos of the rose garden are beautiful – I wish I had known about it during my visit this past summer!! I’ll definitely put it on the list for next time.

    1. Thanks Cynthia! I believe the best time to see the roses is around mid-May to mid-June, when the roses are at their peak. I hope you make it back someday!

  5. I love your pictures! I have heard so many good stories about Portland lately and I really hope to be able to visit this city next time I am in the USA.

    1. Thanks Sanne! Portland may not be the biggest US city, but it certainly has a lot of heart – and good food!

  6. I love the rose test garden! that would be definately something I’d like to check out. I didn’t know Portland was connected to roses in such a way.

    1. I didn’t know much about the roses either until I started planning my trips there. It’s funny how a city can surprise you!

  7. I love cities that offer free walking tours. I find that they are the best way to gain your bearings in a new place and the guides are normally better than some of the paid tours because they work off of tips at the end.

    1. I totally agree Tamason! Free walking tours are the best way to get an introduction to a new city!

  8. Portland looks like a great city. I didn’t visit when i was in the US, but maybe next time. I love free walking tours and have done loads throughout the world, I always think the guides are so good 🙂

    1. I definitely recommend Portland for your next visit, it’d be my second choice after Seattle 😉

  9. Portland is on the top of my American Cities to Visit. Pinned and saved it for when I finally can come there!! Thanks for sharing
    xx

    1. Thanks Nuria! I hope a few of my suggestions help you have as much fun in Portland as I did!

  10. I forgot the word ‘list’ in of my American Cities to Visit ‘list’* am sorry!!

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