Portland

Bridge City, Stumptown, Beervana, or the City of Roses—Portland is as eclectic as its nicknames. The four distinct districts all tout a variation on the theme “Keep Portland Weird.” Southwest houses the downtown city core, a bustling blend of high-profile retail, culture, art, and entertainment. Southeast clings to the Willamette River on its gritty edge, softening into quaint neighborhoods offering all levels of lifestyle. North/Northeast, or “NoPo,” is an evolving, ethno-diverse tract of livability dotted with affordable, hip haunts and a cooler-than-thou attitude. Northwest is the upscale sustainability model anchored by the Pearl and slightly adrift from Uptown/23rd. Together these districts deliver a trendsetting cultural crossroad catering to over eight million visitors a year.

original-portland-banner-crop-2019.jpg

Photo by Elena Kuchko/Unsplash

Overview

When’s the best time to go to Portland?

There’s a reason Portland boasts the highest concentration of craft brewers and distillers on the planet: the rain. Starting in late September, it is a close companion, lasting well into June. That shouldn’t stop you from planning a trip any time of year. Fall boasts colorful scenery and bountiful harvests from local growers. Winter snow is a novel inspiration for intellectual and physical pursuits. Rains relent somewhat in spring, giving way to warmer weather and lingering light. Summer is sensational, with dry, sunny days stretching into glorious evenings perfect for peddling your bike through a happy-hour haze and beyond.

How to get around Portland

Do the 12-mile jaunt from PDX International to downtown on MAX. The $2.50 train ride to the city center takes 40 minutes, providing a great introduction to Portland’s transit environment. The taxi ride takes half the time and runs $40. Amtrak and Greyhound make it easy for West Coasters to drop in.

Skip the car and go by bike, train, tram, streetcar, and bus. A bike gets you everywhere easily, unless you venture into the West Hills for a mile-long uphill slog to the famous Rose Garden. MAX trains are bike-friendly and can enhance your cycling range. You’ll need a car to get up to the mountains, out to wine country, over to the coast, or up the gorge. Some hotels now offer bikes as part of their room package. Bike rentals are plentiful and convenient.

Can’t miss things to do in Portland

Rain or shine, day or night, you can always make the pilgrimage to Powell’s Books. A visit to Powell’s is more than a trip to a bookstore; it’s a literary expedition. The actual need to buy a book is irrelevant. Powell’s is a small city with food, drinks, and entertainment. Oh, and books—rows upon rows of books. The clientele is a cross section of PDX culture, from grandmas to hipsters, students to survivalists. Explore the color-coded rooms to your heart’s content, and then try to find your way out…

Food and drink to try in Portland

Dining in Portland is a remarkably delicious adventure. The fare is focused, local, and sustainably mouthwatering. Start with locally roasted morning coffee. Grab your gluten-free-for-all donut in the food cart pods. Mix up regional and international offerings between lunch and dinner. Do your homework on the food scene and come hungry. But don’t forget to let the spirit move you. With breweries, wineries, and distilleries littering the landscape, it’s easy to find something you’ll absolutely love. PDX turns happy hour into a lifestyle, so carve out that 4-7pm slot on the schedule to make the rounds.

Culture in Portland

Portland’s large reader population enjoys a library and a bookstore that each cover an entire city block. The city is a rich new-media outpost—with film, literature, art, and music spanning the cultural spectrum in a variety of venues and installations. The museum scene offers a full complement of content from art to history, science to forestry, all easily accessible and striving to give visitors context for their NW experience. Note that Portlandia (not the TV show) is the second-largest bronze statue in the United States, eclipsed only by the one on Liberty Island. See it!

Summer serves up some of the most entertaining events on the festival calendar. Cinco de Mayo kicks off the season; then the Rose Festival officially welcomes summer in June. The Waterfront Blues Fest fuels a carefree, all-ages party well into the evening on the Fourth of July, attracting national headliners. The Oregon Brewers Fest puts the beer in Beervana with summer and winter events. Go international with the Chinese, Polish, Italian, Greek, and German festivals. Music/Techfest NW is Portland’s all-out SXSW knockoff in fall. Portland International Film Fest lights up screens in winter. Bottom line—the party’s always pumping.

Practical Information

It’s all about the environment, so always bring rain gear. Pack jacket and pants if you’re planning on going native. Summer can be hot. Winter can bring snow. Fall and spring weather are all over the map, so wear your layers for a comfortable stay. Don’t forget your running, yoga, or exercise wear, and get a workout in. Major-league soccer with the Portland Timbers is a real treat, but tickets are tight, so plan ahead and sit with the “Timbers Army.” Across the river, Winterhawks and Blazers seats are more accessible.

Guide Editor

Jay Rymeski is a veteran writer, producer, and journalist based in Portland, Oregon.

READ BEFORE YOU GO
Six airport terminals in the United States, Europe, and Asia were among those selected in the 2025 Prix Versailles international architecture competition. Not only are these hubs gorgeous, they incorporate innovative eco-conscious design elements, too.
HOTELS
The hotels on this list are as thoughtful about accessibility as they are about design, going beyond compliance to make travel more comfortable and intuitive for disabled guests.
We’re living in the golden age of hotels that have craft cocktails, Instagram-ready design, and in-room turntables. These properties, ranging from West Texan motels to loft-like boutiques in the middle of city noise, are our absolute favorites of the breed.
RESOURCES TO HELP PLAN YOUR TRIP
A slip of a restaurant on Burnside, Canard is the least formal of Gabriel Rucker’s restaurants (Le Pigeon, Little Bird) yet is easily the most fun. The burger is justly celebrated by local critics, publications and even local food notables like former Simpsons writer Bill Oakley, all of whom praise Rucker’s take on the White Castle slider, steamed with onions, pickles, and cheese for $6 apiece. More decadent types opt for the “duck stack,” pancakes with duck gravy and foie gras, topped with a duck egg; or the foie gras dumplings. Canard is open all day until midnight. Because of the limited number of seats and lack of reservations, popping in at an off-hour is a smart move.
Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.
Housed in a converted elementary school dating back to 1915, this sprawling hotel complex has long drawn out-of-towners and local Portlanders alike with its bars, restaurants, miniature movie theater, and even a heated soaking pool that’s open to the public for a small fee. While these amenities—along with the hotel’s sprawling school grounds and proximity to the popular Alberta Arts District—are enough to make it one of the most attractive spots to stay in town, its real cred shines through in the 57 guest rooms, many of which are actually converted classrooms (and still have some of the original scholastic features, such as chalkboards, integrated into the room design). Don’t leave without sampling some of the McMenamins signature brews in the Boiler Room Bar, housed in what was once the school’s boiler room.
Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.
Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland’s most iconic grande dames, and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines.

Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that.
Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property.

The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay.
It’s nice to know I don’t need to get on a plane back to India to enjoy a plate of decent dal in PDX. The Bollywood serves the “people’s food” of India, simple, fresh and undeniably delightful. Most Americans think Indian food is all tandoori chicken and curry. Fact is, these are the banquet foods served only in high-end restaurants or wedding parties on the subcontinent. I was in Assam province in the Spring at a street cafe, eating whatever was being served on the banana leaf in front of me; no utensils, no problem. Except for the warm beer, eating in India is nothing like eating Indian food here, until Bollywood.

There is nothing pretentious about the physical plant. Amid the chaotic decor, aromas from the kitchen fill the place making it all the more homey and inviting. Lot’s of vegetarian options, with a focus on the standby beans and potatoes. The spicing is classic. The plates and cups are metal, much like you’d find on a corner eatery in Kolkata. Order at the counter and have a seat. Get a paneer, a chaat and a dal with a side of paratha to soak up the sauces. They have a short selection of beer and wine and the former is cold and cheap. There are always specials and you should just order them. The plates are small, so if you have a big group, order a bunch. Then sit back and enjoy the ride...
When it comes to pub crawling in Portland, Deschutes Brewing is a classy stop to regroup and recharge in the Pearl. With more than a dozen taps pouring the usual suspects along with a collection of seasonal and experimental brews made specifically for Northwest tastes, the bar has something for every beer lover. The kitchen serves fresh, sustainable fare, including vegetarian and gluten-friendly options. Try the beer-battered halibut or the smoked brisket. The steamed clams with a side of sweet potato fries will also keep you going until your next destination.
Actually, the lobby of the Sapphire Hotel is as far as you’ll get when you visit these days. And for all intents and purposes, it’s far enough. The Sapphire maintains the edge its enjoyed since its inception in the early 1900s. Then a gathering place for the quirky and lightly mannered; cool before cool was cool, it now is the great-grandparent of PDX hip. The candlelit scene keeps the conversation low and the alcohol levels, therapeutic. With cocktails like: You’re Not My Real Dad, Retrosex, Winter Isn’t Coming and Floozie, what could possibly go wrong. The hotel rooms are long gone, but the kitchen still hangs around. The menu maintains a simplicity and charm of another era. An order of the salmon corn cakes with a Sapphire salad will easily sustain, but why stop there. Go for the fully-loaded Sapphire burger, have another pop and regroup for the ginger-vanilla bean creme brûlée. The best thing about the Sapphire is the hang time. It’s out on the bleeding edge of Hawthorne, so once you get out there, you’ll tend to want to linger. The atmosphere encourages it with a sharp wait staff supported by bartenders that roll the dice to delver concoctions you can’t get just anywhere. Happy hour tends to evolve into happy evening, even happy night. I’d say it was a gem, but that would be stating the obvious.
Anyone taking diligent notes on Portland decor is sure to notice similarities in design from location to location beyond a love for taxidermy. Much of that Rose City decorating style emanates from Schoolhouse Electric. Located in a 115-year-old redbrick warehouse and factory building in an industrial part of the city’s West Side, Schoolhouse Electric sells everything from perfect reproductions of 1960s-era IBM clocks to more vintage sconces and analogue clocks than you can shake a stick at. The store’s Ristretto Roasters coffee bar provides a caffeine boost when your energy for curated doorknobs reaches its limit.