20 Hipster Hangouts and Cool Places in Portland

The fun, progressive, eco-friendly and hip Oregon is filled with cool and friendly locals, independent boutiques, creative eateries, artistic neighborhoods and trendy bars.

If you’re looking for the best of the many hipster-approved spots dotted across the city, here are the coolest hipster hangouts in Portland, Oregon…

1. Alberta Arts District – a hip neighborhood filled with local art, live music, bars and restaurants

Alberta Street Portland Oregon

Tin Shed Garden Cafe Portland Oregon

This laid back and vibrant little district in Northwest Portland is a great place to head for a weekend brunch, an afternoon stroll and an ice cream or a browse round a gallery.

The streets are lined with colourful murals and there are plenty of places to enjoy a craft ale or a cocktail al fresco. The Tin Shed Garden Cafe, Great Notion Brewing and Salt & Straw ice cream parlour are just a few of the popular hangouts you can enjoy here.

2. White Owl Social Club – a hip and chilled spot with local beers, vegan food and live music

White Owl Social Club Portland

Southeast Portland’s favourite haunt White Owl Social combines a cool laid back vibe with amazing local brews and cocktails, live music and a huge patio area with a fire pit.

Soak up the alcohol with some tasty but excellent quality comfort food, like tacos, sliders and plenty of vegan options too. Swill them down with a Nectarine Mule and you’re good to go! 

3. Ace Hotel – a trendy downtown hotel which is a beloved hipster hangout

Ace Hotel - best hipster hangouts in Portland Oregon

Cool boutique hotel just a stone’s throw from Powell’s books! All rooms sport gorgeous wall art and some have the extra delights of vintage vinyl and record player, almost everything in the rooms is for sale, you can just take it with you and they’ll add it to the bill.

There’s a Stumptown coffee right next door so your gourmet caffeine fix will be sorted too. Ace Hotel is a hip concept in a gorgeous historical area with plenty of other cool hangouts nearby.

A great place to start on your Portland hipster trail.

4. Hawthorne District – known for its bohemian vibe, quirky gift shops, bookstores, boutiques, live music, hip nightlife and vegan eateries

A guide to Hawthorne District, Portland

Amazing artsy district in Southeast Portland that is just brimming with awesome hipster spots! From vintage clothes to feminist bookshops it’s all here.

There’s a smorgasbord of independent cafes serving delicious food, for example, Jam On Hawthorne, which is always preceded by a big brunch queue but totally worth it.

There’s food trucks, the wonderful Bagdad Cinema where you can enjoy craft beer and movies, great cocktails joints and bold, beautiful street art.

Spend a day just strolling around the area, checking out the cavernous vintage shops and enjoying the independent spirit of the place!

5. Doug Fir Lounge – a cool hipster hangout spot with an eclectic diner menu, bar and indie music shows

Doug Fir Lounge Portland

A super cool, futuristic log cabin style venue within the Jupiter Hotel, the Doug Fir Lounge is a Portland institution with many amazing music acts passing through its doors.

It’s also pretty great for food and drinks too, serving up creative cocktails, Northwestern beers and locally sourced grub which can be enjoyed in the woodsy interior or out on the patio by the fire.

An oldie but a goldie, a not to be missed hip spot to hang out! 

6. The Mississippi Neighborhood – a cool area which has become home to many of Portland’s young, restless and hip

Speck’s Records & Tapes

This quaint historic district in North Portland has good vibes all round! It’s where the locals like to hang out and has all the awesome thrift stores, independent gift stores, eateries, breweries, roasters and record shops that one’s heart desires. Its super cute colonial shop fronts just make it extra gorgeous!

Try Flutter for fabulous gifts and a pet of King the shop cat or browse for hours in Beacon Records. Satisfy your house plant obsession in Pistils Nursery or get prepped for a hike in forest park at Animal Apparel.

There’s hipster brews at Hopworks Bike Bar and award-winning coffee at Albina Press, plus numerous great spots to eat; try Big Elephant Kitchen for really delicious Indian food! Mississippi captures everything we love about Portland, don’t miss (issippi) out! 

7. Jam On Hawthorne – a cool art-filled cafe famous for its hipster vegan brunches

Jam On Hawthorne cafe Portland

You’ll want to make sure you have plenty of space in your belly before you visit this laid back brunch spot; multiple winner of best brunch and with good reason, Jam serves up all your favourites with its own twist (whether you’re vegan or not)!

Try a Nor’wester Omelette or a plate of loaded hash browns and wash it down with a delicious house coffee (especially roasted by Marigold) ….

Just expect to queue, especially at weekends! 

8. The Goodfoot – a much-loved hipster-friendly pub with pool, pinball, bar food, beers on tap, live acts and DJs

The Goodfoot two-level music venue

This cool pub venue is a staple of Portland nightlife and hosts the fantastic Soul Stew, the longest-running DJ dance night in Portland.

The Goodfoot venue is downstairs and regularly hosts great live music, as well as club nights and the upstairs pub, has a great dive-bar vibe with pool tables, pinball machines and Blazers games on the big screen.

It’s an excellent place to meet pals, enjoy proper decent pub grub and cocktails and catch some local art too! 

9. McMenamins Crystal Ballroom – famous venue with vaulted ceilings, grand chandeliers, giant wallscapes and a famous “floating” dance floor

McMenamins Crystal Ballroom historic club

The Crystal Ballroom has been a hipster hangout for more than 100 years! Built in 1914 as Cotillian Hall the building has hosted dance revivals, all man are of folk & blues artists, Jazz musicians and beat poets. Marvin Gaye was here, James Brown was here and The Grateful Dead were here!

Legend has it that Jimmi Hendrix was fired by Little Richard on this very stage.

Since its reopening in the late ‘90’s McMenamins Crystal Ballroom has hosted the best live music shows in town, drawing big names and local talent alike and remaining true to its history by welcoming every new trend through its doors.

It’s proto-hip, it sets the trend before the hipsters even realise it’s being set! 

10. Flutter – a hip offbeat shop selling antiques, jewelry, cosmetics, books, toys and housewares

Flutter Portland Oregon

You can spend hours perusing through the delights of this gorgeous treasure trove of a shop in the Mississippi district and you can be sure a bit of the legendary Portland Hip will rub off on you in the meantime.

Cristin and Sara took the reins in 2006, along with their trusty cat King, and the shop is stuffed with handpicked antiques, reworked vintage clothes, local jewellery, gifts and cards.

The go-to place for something offbeat and unusual, a hip shoppers dream. 

11. Powell’s City of Books – a famous new and used book store for books as well as a cafe and gifts

Powell's Books on Hawthorne - Portland - Oregon

This is probably where you’ll find me to be honest, the biggest bookstore in the states and a cavernous treasure trove of new, used and collectible books with a cafe and a shop to boot, if you need a break from words.

There’s staff recommendations, book signings and ample places to sit and read quietly whilst deciding what to purchase! If you’re lucky you might run into a poet or author, at the very least you’ll be surrounded by people who love books as much as you do! 

12. Cathedral Coffee – a trendy eclectic cafe with coffee, local art, baked goods and occasional live music

Cathedral Coffee Portland

The perfect Portland coffee shop; the interior of this place is amazing, a wooden ceiling crafted to look like the interior of a cathedral soars over comfy velvet armchairs and cosy wooden tables and delicious coffee and tea from local blenders Proud Mary and Jasmine Pearl.

Enjoy house-baked cakes and pastries too and various events throughout the year!

Get on your finest hip vintage gear, grab your iPad and head over to the cathedral, it’s like being in a cool tv show but better.

13. Division Street – now one of Portland’s most dynamic and stylish neighborhoods

Kati Portland Oregon

If you’re a foodie then make this your first stop, the neighbourhood is absolutely choked with hip and delicious eateries! Whatever you fancy you’ll find it here and it will be good!

Go for a melt-in-your-mouth pie at farm-table style Loretta Jeans or gourmet gelato without the queues at Pinolo.

Veggies head to Kati, Indian fanatics to Bollywood Kitchen, for something different the Bimbim Boxes at Kim Jong’s are fantastic.

For something with a German twist head to Olympia Provisions and hang out on the sprawling patio with amazing Weiss Beer and Charcuterie. Your belly will thank you forever! 

14. Red Light Clothing Exchange – a shop selling men’s and women’s modern and vintage clothing in a vast, funky space

Red Light Clothing Exchange

Vintage lovers like me can literally spend a day in this cavernous vintage treasure trove on Hawthorne.

From cowboy boots to wedding dresses and everything in between you’ll find it here and the pricing is super reasonable too!

There’s grungy jumpers that the ghost of Kurt Cobain will be coveting from the beyond, silk and fur combos that would do Courtney proud, fit and flares, 70,s maxi’s hammer pants and creepers…perfectly curated and laid out in such a way that everything feels like a discovery!

Red Light has been an anchor on the corner of Hawthorne for more than a decade and with Portland’s hipster scene in full flow, I’m sure it will be there for many more years to come! 

15. Belmont Street – a popular area in southeast Portland with a strong sense of individuality

The famous Stumptown Coffee Roasters in downtown Portland

Just round the corner from Hawthorne you’ll find Belmont Street, another cool and unusual shopping destination!

Get a cup of coffee from the original Stumptown Coffee Roasters and then hit the vintage shopping starting with Mix Tape, where you’ll find wonderful restyled vintage pieces and restored leather.

Next up, for gender-bending and inclusive vintage buys, head for Planet X Vintage and then top it off with a trip to quirky Naked City Clothing for all things cute and kitschy. 

16. Boxcar Pizza – a cool vegan eatery housed in a unique building 

Boxcar Pizza Portland Oregon

The tag line for this place is ‘Hip Cats, Square Pies’… I don’t know if I can do better than that! An amazing all-vegan Detroit style pizza kitchen in the Portland Zipper building.

House-made vegan cheese, tons of gluten-free options and just a super hip and tasty place to swing by for a bite! 

17. Dig A Pony – an impressive barroom and hangout located in the heart of southeast Portland

Dig A Pony Portland

Super cool bar venue in southeast Portland, the central circular bar invites plenty of socialising and conversation whilst the cosy old-style leather booths are perfect to hide away with a group of your favourite people.

Dig a Pony has a great atmosphere every night of the week with plenty of events and clever music nights like ‘Hostile Tapeover’.

The bar serves great cocktails and a wide variety of homegrown ales and food is provided by Stevens Italiano, straight-up no-nonsense tasty.

There are vinyl nights, great artwork on the walls and a fab fusion of old and new in the decor. Perfect spot to meet friends and make new ones! An all-round good time! 

18. Gold Dust Meridian – a happening spot for creative cocktails, bar food in a hip room

Gold Dust Meridian Portland

Back on Hawthorne for ‘Creative Cocktails and elevated bar food’ at Gold Dust Meridian. It looks pretty unassuming from the outside but inside you’ll find some of the best cocktails in town and plenty of hipsters enjoying them!

It strikes a great balance, managing to be hip yet unpretentious, exclusive yet friendly, delicious yet affordable.

We started here one night for a bit of a bar crawl and enjoyed it so much we didn’t crawl anywhere else at all! I

nstead, we sat at the bar and chatted with the friendly and knowledgeable barman, nibbled on some tasty gourmet bar snacks and enjoyed several innovative cocktails in a cosy, warm environment!  Highly recommended!

19. Proud Mary Cafe – a hip and modern cafe set in an industrial-chic space offering craft coffee, breakfast and smoothies

Proud Mary Cafe Portland

Located in the aforementioned Alberta Arts District you’ll find the original Aussie-owned gourmet coffee cafe Proud Mary. It occupies a cool industrial-chic space, plenty of chrome and exposed brickwork, and serves up the best coffee in town.

Home roasted creative blends like Lazy Sunday, Intergalactic and Exploding Heart are served up by hip baristas alongside delicious, locally sourced food. From humble beginnings, the Proud Mary Blends are now served in several places throughout the city and are available to buy online too.

The best place to sample these brews is still to head for the mothership and enjoy savouring the flavours in the hip environment with all the other coffee snobs! 

20. Music Millennium Vinyl Shop – a hip record shop selling LPs and CDs spanning multiple genres

Best record stores in Portland

Right by the famous ‘Keep Portland Weird’ mural you’ll find Music Millennium. Serving the city’s Muso’s since 1969, you can’t get hipper than this!

Browse the aisles of vinyl, both old and new and pick up something for your collection or check out an in-store Q&A, signing or gig with amazing musicians.

This store is the oldest operating music store in the Pacific Northwest and a not-to-be missed opportunity to chill, browse and chat with fellow music heads! 

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