ANY NEWCOMER to Portland needs to first do as Portlanders: Relax, smile, and finish your cup of coffee. Portland is no megalopolis, so there is no need to panic about getting from here to there with enough time to spare for this and that.

However, as each of our neighborhoods has their own flavor, it’s super helpful to know what you are looking for in your first visit. Looking for someplace charming and laidback? Young and hip? Rambunctious and unpredictable? Artsy and affluent? Industrial and sexy? Portland is here to serve, as is this list of its best neighborhoods and why you should stay in them.

Where not to stay in Portland

Let’s narrow it down by starting with where NOT to stay. Despite our professed love of bikes and streetcars, Portland does not yet have the convenient mass transit of New York or Barcelona, so there are a few areas that should be avoided for convenience’s sake.

First, avoid the deep Southwest neighborhoods of Hillsdale and Multnomah, which are farther away from downtown than they appear and will not save you that much money.

While Southeast has its own delightful and funky neighborhoods like Sellwood and Woodstock, it’s best to stay north of Highway 26/Powell Boulevard if you are looking to explore the West Side attractions (this is unless you can find an Airbnb within a few blocks of the MAX Orange Line).

Most of East and near-Northeast Portland is well connected to the city center by bus or streetcar, but it generally helps to stay west of Cesar Chavez Boulevard Ave. and south of NE Killingsworth. When it comes to the West Side, stay east of Skyline Boulevard and south of Slabtown to get easier access to the city center.

There are plenty of interesting neighborhoods outside the radius I just laid out (including St. Johns in North Portland), but if you are new to the city you are going to want to spend as little time getting around as possible.

It’s important to note that Portland is not that big and that you can drive across the whole thing in half an hour. Our blocks are small and relatively orderly, so getting lost isn’t easy and we are very tourist-friendly (ask us directions!).

The 5 coolest neighborhoods in Portland

1. Pearl District

Photo: Sean Davis

What was a handful of beat-up warehouses, desolate rail yards, and brewery brownfields before 2000 is now Portland’s new playground for high-rises, boutique shops, immaculate parks, and brewpubs. The Pearl takes its name from a legendary Portland party host who also made her name as a patron of the arts and social causes around the world. Even after being dressed up by Portland’s urban elite, the district still reflects Pearl’s cosmopolitan and creative vibes, making it the perfect destination for arty types looking for famous cuisine with a Portland twist.

The Pearl is home to the world-famous Powell's Books , which occupies an entire block right at the southern edge of the neighborhood and serves as its cultural gateway. After picking up a copy of Chuck Palahniuk’s Fugitives and Refugees, or Ursula Le Guin’s Lathe of Heaven (both Portland-set classics), head north into the “Brewery Blocks”, which form the hoppy “heart” of the neighborhood thanks to Oregon favorites such as Deschutes, Bridgeport, Rogue and 10 Barrel Brewing .

While each brewery offers the very best of northwest IPAs, the highfalutin small-plate menus of Oba Restaurante , Mediterranean Exploration Company, Irving Street Kitchen, Piattino, and Zaatar restaurants will show you just how impeccable world-inspired cuisine with Northwest ingredients can be. For some quick lunch/happy hour tapas, step into Andina for their yucca croquetas or their pimiento piquillo relleno.

After sipping some Latin American wine, stroll over to public parks Jamison Square and Tanner Springs. These spaces were designed to reflect Portland’s renowned urban development philosophy, making them two of the most Instagram-able spots on the West Side. On a hot day, you can cool your feet off in Jamison Square’s interactive fountain — but watch out for the local kids splashing about.

The art scene cultivated by Pearl lives on in her namesake’s rich spread of art galleries and shops. Exhibits range from hand-blown glass pieces at Bullseye Projects to contemporary paintings at Annie Meyer, and images from the Northwest’s best photographers at Blue Sky. Looking to contribute your own creative vision to the Pearl’s art scene? Visit Work/Shop to build up your watercolor skills (classes range from $8-$60). You can even enroll in the Pacific Northwest College of the Arts!

2. Nob Hill

Also known as the “Alphabet District” or “Northwest”, Nob Hill has long been beloved for its quirky Victorian homes and tasteful early 20th-century apartment buildings. While there is certainly a Haight-Ashbury/Greenwich Village vibe to it, Nob Hill stands out as uniquely Portland thanks to its century old trees lining slim avenues bustling with gutter-punks, frat bros, art students, high-end shoppers and sometimes my grandparents. This makes it an ideal candidate for someone looking to make new friends at a high-end hostel or pool hall.

Stretching from the neighborhoods of Goose Hollow and Slabtown are Nob Hill’s two core avenues: NW 21st and NW 23rd (nicknamed “Trendy-Third”, at times pejoratively).

NW 23rd is a high-end shopper’s paradise. A smattering of big-name stores are surrounded by local boutiques such as Hip Hound for holistic pet owners, Himalayan Arts and Handicraft for top-of-the-world bric-a-brac, and Oh Baby Lingerie for, well, you know. In between the little shops are popular eateries that serve the best slice in town ( Escape From New York Pizza ), the best American steak (Papa Haydn), and the best scoop of ice cream ( Salt & Straw ). If all that shopping is wearing you out, take a pause over a hot cup of oolong in the upstairs lounge at Tea Chai Te.

Despite being only two blocks away, NW 21st has its own vibe, which tilts more towards evening entertainment. Start with a matinee Cinema 21, which was the first indie-theater in Portland to have regular screenings of The Room and still shows local independent films.

While 21st is packed with affordable restaurants carrying cuisines from just about everywhere, Marrakesh is the only one to accompany the food with sounds and dancing from its native country (Morocco). Chase that tagine down with a top-shelf glass of whiskey from either the Pope House or North 45 before heading into The Pharmacy to play every bar and board game ever created (including a game of giant Jenga).

For those not interested in dropping a dime in one of Portland’s prettiest neighborhoods, consider a casual stroll between architectural masterpieces on NW 22nd. Wallace Park off 25th is famous for the tens of thousands of swifts that fly into a nearby chimney each autumn — it makes for a fantastic destination any time of year.

3. Boise

What was a predominantly African-American neighborhood due to racist redlining in the mid-20th century has seen rapid gentrification in recent years, resulting in plenty of mixed feelings among both new and old residents. Like most of Portland’s most popular neighborhoods, Boise’s history is preserved in the century-old Foursquare-style homes, a few old shops, and in the actions of community organizers. Thanks to the latter, there are few neighborhoods in Portland as diverse and successful as Boise. For travelers looking for the feel of old Portland without giving up the amenities of the new scene, Boise has plenty of quiet streets lined with charming guesthouses.

Boise is centered on Denorval Unthank Park, named after a prominent black civil rights activist from the 1960s, and is flanked by N Mississippi and N Williams avenues, where visitors will find most of the neighborhood’s hotspots.

While Mississippi is still defined by its mix of old and new low-rise buildings, new apartments and venues have sprouted up and down Williams, giving it a modern sleekness uncommon on the East Side. Still, the avenue carries on its manufacturing tradition with spots like the United Bicycle Institute, which offers classes on how to construct one of Portland’s favorite form of transportation. For those looking to browse or buy a two-wheel work of art: try Portland Bicycle Studio, which has what I consider to be the best collection of bikes in the city.

After sprucing yourself up with a close shave at Cloak and Dagger and a mind-clearing session at Yoga Shala, head over to Mississippi for a Pacific Northwest-oriented dinner at Quaintrelle, whose menu is constantly changing according to what’s in season, or the Olympia Oyster Bar. Keep walking down Mississippi and you are sure to come across a live music venue bumping the sounds you want to dance to, whether it’s jazz at The 1905, salsa-nova at Mississippi Pizza, or rock at Mississippi Studios.

4. Central Eastside

Directly across the Willamette River from downtown Portland is a district famous for its contradictions. At once industrial and upscale; dense and underutilized; cut-off from its surroundings yet central to life in the city — this neighborhood is where everything happens despite it all. The Central East Side is for the traveler looking to do anything and everything urban, from clubs and restaurants to shops and museums, and who doesn’t mind the sounds of the nearby freight train.

While this neighborhood is famous for its vibrant nightlife scene, it is also bursting with family-friendly activity, starting with the Oregon Museum of Science and Industry, or
OMSI . After a visit to Portland’s planetarium and a hop on a nuclear sub, rent a Kerr Bike right outside OMSI’s doors and take a self-guided tour along the Eastbank Esplanade , which will give you top notch views of the Rose City and her steel drawbridges. For those interested in the bizarre side of Portland, visit Kidd's Toy Museum or, even stranger, Stark’s Vacuum Cleaner Museum.

For lunch, try the Japanese ramen at Boke Bowl before heading into the industrial area’s quirkier warehouse shops. Lippman Co. is every local’s favorite spot to pick up party outfits and decorations on the cheap and is plenty entertaining for just a visit. There is also Next Adventure, Portland’s biggest outdoor store (when measured by adulations from locals), and Guardian Games , which seems to carry every board and tabletop game ever imagined.

When it comes to eating and drinking, there are too many spots in CES to list, but it is always important to note that it has plenty of brewpubs (Base Camp and Burnside Brewery are perhaps the best). For my money, nothing beats a Cajun dinner at Le Bistro Montage, which might be the only place in town where you can get gator bites next to jalapeno macaroni and cheese.

Of course, you are going to have to dance like crazy to burn off those calories. Nearby Bit House and Dig A Pony are just two of the countless nightclubs where you can dance to funk and house music while making new friends.

5. Old Town/Chinatown

Despite being made up of only a few dozen of Portland’s tiny city blocks, Old Town/Chinatown takes everything old and new in Portland and smashes them together in a wild bouquet. A preposterous mélange of three story cast-iron façades about Portland’s most iconic skyscraper, Big Pink (aka US Bancorp Tower), in a neighborhood that almost defiantly tells the whole story of Oregon’s biggest city, from its rough frontier beginnings to its gilded present day.

While this neighborhood is still rough around the edges, its convenience to the party and music scenes at night and city parks and galleries during the day makes it the ideal candidate for the adventurous traveler looking for stories to tell.

Old Town/Chinatown straddles Portland’s dividing line between north and south, Burnside Street, and curves like a Cheshire grin against the Willamette River. This setting makes the neighborhood the most visited attraction in Portland, with local staples such as the Voodoo Doughnut , Stumptown Coffee Roasters, and Kells Brew Pub anchoring its core.

But there is more to this neighborhood than its most renowned vendors of haute cuisine (yeah, our donuts are elite). Newcomers must begin with a visit to Waterfront Park Trail and the Saturday market (or any one of the countless events and festivals held there, including the Oregon Bite and the Oregon Brewers Festival). Those looking to learn about Oregon’s history should visit the Oregon Nikkei Legacy Center (which tells the story of Japanese-Americans), the Oregon Jewish Museum, and the Maritime Museum (which is located on an old-timey paddle boat tug).

While “Chinatown” often feels like a strong word for a few blocks featuring little more than painted street lamps, the Lan Su Chinese Garden is a little-known treasure and restaurants House Of Louie and the Republic Café combine your classic Chinese-American flavors with distinct atmospheres.

After dark, it would be borderline sinful for lovers of the nightlife to avoid the boisterous Ankeny Street. The Shanghai Tunnel Bar blends local folklore with some tasty pub eats; the new Paris Theatre offers contemporary music acts in a burlesque-y setting; and Ash Street Saloon is still the preeminent rock venue for downtown Portland (although nearby Dante’s is a close second).

While in the area, be sure to drop a nickel in the Skidmore Fountain, which was originally designed to pump free water for the debutantes and debauched alike.


To find some of these places, check out our travelstoke map:

 
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