Portland, Oregon is an exceptionally friendly city. Baristas ask you how your day is going and then give you their undivided attention as they await your answer. Drivers always yield to bikers and pedestrians, and are known to wait patiently (sometimes infuriatingly) at intersections waiting for the other driver to go first. But knowing which neighborhoods are worth your while can be less visitor-friendly. That’s because there are officially 125 neighborhoods in PDX in five different “quadrants” (that’s right…five, not four!). NE, NW, SE, SW, and the bonus area of North Portland. So while there may be a lot of micro-nabes to choose from, these are the top hotspots on the east and west sides of the Willamette River (which bisects the city) for shopping, staying, eating, imbibing and exploring.
If you’ve already heard of one neighborhood in Stumptown, chances are it’s the Pearl. After all, the formerly grungy warehouse district next to downtown is now the city’s most polished gem (think of it as Portland’s version of NYC’s SoHo or DUMBO). It’s densely packed with luxury high-rises, high-end clothing and home shops, and pricey salons for those in need of a mani/pedi or rocker-chic haircut. There’s no shortage of farm-to-table restaurants and cocktail bars, either. But you’ll also still find scrappy Portland stalwarts like Powell’s Books, a fiercely independent “City of Books” that’s anchored the neighborhood since 1971. If it’s your first time visiting, use Powell’s as your starting point and wander the Pearl from there by heading away from busy West Burnside — it’s one of Portland’s most walkable neighborhoods.
You’ll find the bulk of the city’s hotel options downtown, ranging from classic (The Heathman), hipster (Ace), trendy (The Nines), and lots of great options that somehow manage to toe the line between all three categories (Dossier, Monaco, Lucia, and Modera, which are housed in historical buildings but have modern interiors). At the epicenter of downtown is Pioneer Courthouse Square, where you might stumble across a rock concert, political protest, holiday tree lighting, or Feast Portland food festival event, depending on the day. Hundreds of food carts are concentrated in this area, making the options for cheap eats endless. Check out what’s on exhibit at the Portland Art Museum or what performances are coming to “The Schnitz” (AKA Arlene Schnitzer Concert Hall). On Saturdays, do not miss the farmers market on the Park Blocks on P.S.U. campus. Bursting with PNW bounty and stellar ready-made eats, it really is one of the country’s best.
One of the Rose City’s best shopping streets is Northwest 23rd street, where charming shops and cafes line a stretch of about 20 blocks between Burnside and Vaughn streets spanning the Nob Hill/Alphabet/Northwest districts. Look for small, independent Portland retailers like Betsy & Iya jewelry and Manor Fine Wares, plus national brands including Free People, Williams-Sonoma, and Kiehl’s. And if you’re looking for a neighborhood to take advantage of Portland’s ubiquitous happy hour deals, this is it (many restaurants actually have two! Typically something like 4-6 p.m. and 10 p.m.-close). It’s easy to stroll between favorites like St. Jack, Fireside, Matador, Bamboo Sushi, and 23Hoyt slurping down the specials.
Southeast Division Street was fairly sleepy until Pok Pok came around. But Andy Ricker’s Asian BBQ joint — run out of his house — put both the street and Portland on the country’s culinary map. A zillion chicken wings, several restaurant expansions to NYC and LA, and a few James Beard awards later, the O.G. Pok Pok is still delivering a can’t miss menu of Thai-focused dishes. (If there’s a wait, walk across the street to its sister restaurant, Whiskey Soda Lounge, for cocktails and wings). Now the street reads like a greatest-hits of PDX dining. You’ve got Salt & Straw's famous ice creams, Ava Gene’s modern Italian cuisine, Lauretta Jean’s amazing pies, Indian street food at Bollywood Theater, and a slew of cute spots to belly up to a bar or peruse locally handmade gifts.
A few blocks east of the Willamette, you’ll find the Jupiter Hotel and Doug Fir Lounge, a hip (but without trying too hard) hotel with neighboring live music venue that helped make Portland’s east side cooler than it’s west side. It’s the major landmark on this stretch of East Burnside Street, where you’ll find everything from tattoo parlors and strip clubs to rock-climbing gyms. Stop into delightfully divey bars like Sandy Hut (just a block north of Burnside on Northeast Sandy Boulevard), and truly top-notch eateries including Le Pigeon, Canard and Tusk, plus some of Portland’s best fried chicken at the perpetually busy Screen Door.
See that green hump in southeast Portland as you look towards Mount Hood? It’s an inactive volcano just 60 blocks from downtown called Mount Tabor. It's where locals go to play tennis, jog around the reservoir, and — on a clear day — catch views of the city skyline and west hills from one side, “the mountain” to the other. (It’s also where the fun, boozy ridiculousness known as the Adult Soapbox Derby goes down every summer.) After your sweat session, reward yourself with breakfast, lunch or dinner at neighborhood favorite Coquine, which is just a couple blocks away. No matter what meal your order, getting some chocolate chip cookies to go on your way out is practically a city ordinance.
For fifty-some blocks starting at the Willamette River and going east, all of Southeast Hawthorne Boulevard is dotted with some of the best of what Portland has to offer. We’re talking vegan eateries, cideries, perfumeries, doughnuteries, fresh-pressed juiceries…basically all of the “ies.” Some stretches are more walkable than the rest, but the area around the historic Bagdad Theater is the best for strolling. You can’t miss the beloved Portland landmark — just look for the theater’s vintage neon sign looming high on Hawthorne and 37th. Don’t be dissuaded by the patchouli vendors (remember, the dream of the '90s is still alive in Portlandia!). There’s good stuff to be found here, and it’s a quintessentially Portland experience.
Another scrappy PDX neighborhood that’s come into its own is North Mississippi Avenue, now a legit destination for live music, shopping, dining and drinking. The popular retail area is only five long blocks long, but it’s packed with Portland goodness. In the mood to shop? Delight in The Meadows, a tiny jewel box filled with finishing salts, chocolates, bitters, wine and fresh flowers (nothing else), or Pistils Nursery, where succulents, ferns, and exotic plants fill every crevice and corner. Hungry? Grab tacos at ¿Por Qué No?, bivalves at Olympia Oyster Bar, comfort food brunch at Gravy, or ice cream at Ruby Jewel. Or, settle in for four artful courses of seasonal PNW fare at Quaintrelle — an absolute steal at $65 considering how fresh, refined, and inventive each and every plate is. Feeling parched? Interurban, Prost, and StormBreaker Brewing will quench that thirst.
Alberta Arts District
Tiny houses, food carts, art galleries, coffee bars, and breweries line funky Northeast Alberta Street, putting it in the running for the most-Portland Portland neighborhood. The action runs for about 20 blocks starting at Northeast 10th street. Sample the global cheap eats from an eclectic mix of restaurants on wheels, catch a show at the sweet Alberta Rose Theater, and shop independent clothing and home boutiques. If you’re really digging the vibe, see how much fun you can have in 150 square feet at one of the Lilliputian house rentals. If you visit in summertime, the neighborhood hosts a boisterous and fun art walk the last Thursday of every month.