Portland, Oregon is a gem in the west, a familiar hipster haven with an affection for the outdoors. Artisanal crafts, coffee, and cocktails enliven the quadrant city, all to the rhythm of an entrepreneurial flow which emboldens such creativity and ambition. Use the locally-built app WorkFrom to join the remote working force of Portland where literally every café is ranked by WiFi, seating, outlets, and grub. Even laundry facilities in Portland are stylized and serve coffee.

The mood here is happy. It’s where intellectuals find themselves in sleeveless fleece zip-ups trail running in America’s largest urban forest. A floppy hat with low Frye boots will get you everywhere else you need to go — that and a raincoat.

The trees light up in autumn in shades of red and piercing yellows. With numerous quaint residential streets, each neighborhood has its own main drags with all the mainstays you could hope to find yourself on a Sunday afternoon.

The Willamette River divides the city east and west, and Burnside Street divides it north and south. There are still so many locations left to explore, sip, and shop — but from our best due diligence, here’s your sauntering guide to Portland, Oregon.


Alberta Arts District

A post shared by BoxerRamen (@boxerramen) on

Located in the Northeast quadrant, NE Alberta Street is the main artery of this lively and artistic neighborhood. Visit Digs Inside & Out, offering free espresso to all shoppers and Red Sail — these are design shops that you will want to move into. Grab lunch at Boxer Ramen. Sip coffee and enjoy the lemon poppy seed cake while you work remotely at Case Study or grab an afternoon libation at one of the outdoor patios when the sun comes out to play.

Alberta Arts District on Roadtrippers



Also located in Portland’s NE quadrant, visit Mississippi — a slightly more youthful area compared to Alberta Arts District, filled with tons of awesome and affordable clothing and vintage shops and heaps more bars. Check out The Annex,  Animal Traffic, and Worn Path for your quests in attire, not to mention outdoor goods from brands like Frost River.

A post shared by WORN PATH (@wornpathstore) on

If you need to pick up a gift or restock your bar, check out The Meadow — it’s a small shop covered wall to wall in artisanal bitters, salts and chocolates from around the world, not mention a wide assortment of salt blocks and bowls. In case you need to step out of the rain, grab a drink at The Rambler.

Mississippi on Roadtrippers


Belmont & Hawthorne

The southeast quadrant of Portland has a few main arteries dubbed as restaurant rows including Division Street and Hawthorne Boulevard. Grab brunch at The Woodsman Tavern or sip brew at Stumptown Coffee. Amazingly, numerous old time theaters are preserved and scattered around town playing to small houses packed in for anything from an indie flick to The Martian. There is also a village for all intense and purposes of food trucks at SE 28th Place & Division Street.

West of the Belmont – Hawthorne area is East Portland, just along the Willamette River and north of Portland’s neighborhood called Brooklyn. Here there are industrial loft spaces converted into more coffee houses as well as the Grand Marketplace. Also south toward Brooklyn is the Creston-Kenilworth neighborhood near Reed College where the main drag SE Gladstone is home to a few bars and restaurants including C-Bar — a pub with a huge beer menu, delicious food, and an entire back room devoted to pinball.

Belmont & Hawthorne on Roadtrippers


Pearl District

DSC01782-1edited 123
In the Pearl District

The Pearl District is located in Portland’s downtown and is downtown’s pearly gem. Brick loft spaces with tall ceilings and luxury condominiums line the cobblestone streets of this small, chic hood. Get lost in Powell’s City of Books—aptly named and potentially one of the largest I’ve seen; plus it happens to have some really cool swag. Check out locally made crafts — everything from jewelry, to bags, to an ice-breaking hatchet to canoe paddles — at Made Here PDX and then head over to Hunt & Gather for more home goods.

A post shared by MadeHere PDX (@madeherepdx) on

One thing immediately apparent about Portland and its creative contingent is that the cost of the city — from food to drink to real estate — is low compared with its cool sister cities, and so creativity can persist here because people can afford to see what they are capable of.

The Pearl District on Roadtrippers


Forest Park

Flânerie need not only exist on city sidewalks. Portland’s Forest Park is the largest urban park in America with more than 80 miles of trails tucked into a gorgeous, green mountainside with creeks and wild flora. I went for a jog down and then back up, experiencing only a small piece of this epic park near to Portland’s Audobon society outpost —and it was dazzling!

If you enjoy this guide to Portland, you can take it with you. Using the GPSmyCity app guides can be downloaded to your phone for offline use.

Download it here.

By the way, if you do download it, I’d love to hear from you. Did you enjoy using GPSmyCity? I want to make sure scouts and findings on Maidstone Buttermilk are as helpful to you as possible.