The Ultimate Portland Travel Guide

Point is, it's not all roses in the City of Roses. As many residents bemoan the disappearance of “Old Portland,” these topics are likely to come up. Listen, but unless you're well versed, maybe don't weigh in, lest you get a strongly worded note hand-delivered to your hotel room.

Honestly, Portlanders are more prone to write passive aggressive notes when they're miffed than to punch anyone (except maybe Nazis). That said, don’t ride your bike or scooter on a busy sidewalk. Avoid saying "put a bird on it" or some dumb Portlandia shit. Don't litter. Tip strippers $1 per song and bartenders at least $1 per drink. When in doubt, follow the immortal words of Abraham Lincoln: Be excellent to each other. (And party on, dudes.)

The best time to visit Portland

The myth that it rains for nine months out of the year is total bullshit. It's only seven. But that relative slog of gray skies and damp clothes makes May-October absolutely stunning. Late spring/early summer is when Portland turns into an earthly utopia of deep greens, temperate and sunny days, and clear skies, transforming the city and its surrounding areas into one sprawling playground.

Fall's no slouch, either, with the cooler climate giving way to beautiful colors and mandatory trips to nearby Sauvie Island for pumpkin patches and hayrides (it's a rite of passage). Winter has its charms, too: There are breaks in the rain, things are generally less crowded, and nearby Mt. Hood becomes a destination for skiers and fans of The Shining, which shot its exteriors at the historic Timberline Lodge. But if you happen to be in Portland proper when a rare bit of snow falls, be ready for the long haul: More than an inch generally shuts the entire city down.

How to get around

The spankin' new fleet of rentable e-scooters that hit the city earlier this year has replaced the bright-orange Nike Biketown rental bikes (think Citi Bikes, but uglier) as passive-aggressive Portlanders' favorite thing to get unreasonably angry about, but both are readily available for convenient rental. You can also rent a bike from a place like Cycle Portland or Everybody's Bike Rentals for the same results without the stink eye.

Beyond two wheels, the MAX lightrails jaunt to most of the major metro areas (and suburbs) and are easily navigable, and a fleet of buses can get you to your final destination if you're not in a big hurry. If you're tired of walking downtown or near the river on the east side, the Portland Street Car can get you close to where you're going, provided where you're going is in a very small radius. For maps and trip planning for all of these, download the app for Trimet.

Otherwise, most destinations are a short Lyft, Uber, or cab ride away. Just don't expect to easily flag a cab down if you're app averse: You'll want to call Radio Cab or Broadway Cab to schedule a pickup.

How to order food and booze

People have been ordering food and booze the same way for centuries, but of course Portland complicates things. Many restaurants -- even the nice ones -- go for the counter-service model, where you order your food, take a number, and sit down. You'll be asked to tip up front, usually with a pre-populated 20% on the tablet, which is weird since you're being asked to bus your own table. You don't have to go all-in there. But it's appreciated.

Also, at bars you'll notice a very weird Portland phenomenon: People line up to get their drinks like they're waiting to go on a Ferris wheel. It's odd. It's obnoxious. And bartenders seem to hate it, going so far as to put up signs that say "do not form a line" -- signs people form lines underneath. Make like a normal person and just go up to the bar. You'll get your drink quicker and your bartender will be relieved.

How to survive a strip club

It's really, really hard to explain Portland's bizarre strip club culture, but just know there's a strong chance you'll be in one at some point. Be cool. The vibe here is like chilling at a bar where there happens to be naked people. Some, like the vegan vampire-themed Casa Diablo and the steakhouse strip club Acropolis, have great food. Others, like Sassy's and Union Jack's, have multiple stages that seem more like Suicide Girls-themed Cirque du Soleil. Mary's has history (and often roller skates). On Sundays, punk rock club Devils Point has Stripparaoke (it's exactly what you think it is), while places like Silverado bring the Magic Mike thunder. Just go with it, remember to keep your hands to yourself, and throw those dollars (never, ever make it rain quarters).

How to do the reefers

Recreational dispensaries are so prevalent that there are often workers outside spinning signs for $5 grams as if they were shilling Hot N Readys. It's great. If you see a big green cross on a building and are 21, you can purchase buds, edibles, drinkables, and everything in between. You'll be carded, then likely directed to a waiting area before gaining access to the wonderland that is the dispensary.

Ask questions: Budtenders are there to help. Just don't touch anything: You can't actually handle the merchandise until you've paid (which you can usually do with cash or debit). After that, if you're smoking you can't do it in public or in hotels. Check the rules of your Airbnb before lighting up, and if you decide to forego the rules (which people do indeed do), know that you can still get pinched, same as you can anywhere else.

How to own the LBGTQ night life

Portland is one of the LGBTQ-friendliest cities in the US, to the degree that it’s almost surprising “The Rainbow Connection” isn’t the official anthem. Most every bar and restaurant is extremely welcoming, with many venues throwing down on regular queer nights. Even local movie houses are in on the action, with events like Hollywood Theatre’s Queer Horror series and the longest running Rocky Horror night hitting the Clinton Street Theater every Saturday. The city’s equivalent of Boys’ Town is a triangle of SW Portland colloquially known as Vaseline Alley, home of iconic bars like Scandals, and though it's ground zero for Pride Week, it's a drop in the bucket for the city. Downtown’s CC Slaughters is the de facto night club for sweaty dance parties, while drag revue Darcelle XV has become as much a Portland icon as anything else. On the east side, the atmospheric Crush offers craft cocktails to go with buzzy DJ-fueled nights, and things get decidedly more risqué with Silverado, the gay strip club, and at The Eagle, a divey bear bar in North Portland known for naked pool. Regardless of where you are, though, you’ll very likely feel welcome.

Downtown

Much of Portland is a hotel desert. Not downtown, though. It’s the best bet for people who want amenities while remaining close to pretty much everything, including the much-hipper east side just across the river. Walkability is unmatched, with dozens of acclaimed restaurants, the bro-y nightlife of Chinatown, the city's best food carts, and the iconic Saturday Market all within walking distance. You’re also by the main hub of public transit; the Pioneer Courthouse Square -- aka Portland's Living Room -- serves as the city's super-chill version of Grand Central.

The hotels here run the gamut from the ultra-hip original Ace Hotel, which also houses legendary cocktail restaurant Clyde Common, to the old-school (we're talking Beefeaters as bagboys) Heathman, to the luxury digs at The Nines, which includes steakhouse Urban Farmer and the rooftop bar at Departure. Boutique hotels like the Hotel deLuxe and the newly renovated Sentinel abound.

Central Eastside

Right across the river from Downtown, Central Eastside is slowly transitioning from skid row to Portland's next big neighborhood, with restaurants like vodka-soaked Russian destination Kachka and world-famous Le Pigeon drawing crowds right along with a handful of great breweries (Burnside, Upright, Hair of the Dog) and bars ranging from swanky to skanky.

The converted Jupiter Hotel is ideal for folks who want their hotel package to include a party thanks to the neighboring Doug Fir Lounge, a legendary bar and music venue. Bougier digs are available down the road (a short street-car ride from the action) at Hotel Eastlund. It's the perfect antithesis to downtown, a still-slightly-rough under-the-bridge area that includes the best in food and drink, easy access to the (must visit, honestly) Oregon Museum of Science and Industry, and a taste of the hipper-than-thou Portland you're likely thinking of in the first place.

Alberta Arts District

With more than 30 bars and restaurants in a scant 15-block radius, Alberta Arts was an early adopter of Portland's burgeoning food scene (and many would argue the first victim of gentrification). You’ll find a wealth of Portland's best and brightest crammed onto the street, from fusion star Aviary and Indian crossover Bollywood Theater to the long lines at ice cream mecca Salt & Straw, instantly iconic hazy IPAs at Great Notion Brewing, and the granddaddy of Portland's now-great BBQ scene over at Podnah's Pit.

Airbnbs are aplenty here, though the area's only hotel is a doozy: The Kennedy School is an old elementary school that's been converted into a sprawling campus that includes a brewery, several bars, a restaurant, a movie theater, and a hotel where the quarters are old classrooms.

Mississippi Avenue

The Mississippi/Williams corridors -- technically referred to as King -- are the next iteration of Alberta, but somehow more walkable and manageable. In a tiny radius, the area packs an unfathomable amount of Portlandness into a few square blocks, including must-try brunch destinations Tasty n Sons and Sweedeedee; breweries like Ecliptic and Stormbreaker; multiple cart pods, including one outside German beer hall Prost that includes the city's best BBQ in the form of Matt's; and more.

Still doubting the Portland cred? This is an area where a boutique taxidermy emporium exists a block from a place that only sells lightbulbs, which is right next to an indie music venue, a salt store, and a synthesizer shop. Do NOT be lured by the many hotels across the walking bridge from the neighborhood: They're generally fleabags. But the Airbnb options are strong here, and include tons of tiny houses.

The Pearl District/Alphabet District

Not all of Portland's hipness includes tallboys and the scent of American Spirits: The Downtown-adjacent Pearl District is Portland's answer to the bougie downtowns of most other cities, a maze of high-rise apartments, upscale restaurants, lauded Oregon breweries (Von Ebert, Deschutes, Rogue, Bridgeport), and very trendy bars. It butts right up against the Alphabet District, which is basically the fancier version of Alberta Arts, with the "Trendy Third" stretch of NW 23rd packing in an impossible number of boutiques and ultra-hip shops. You’ll also find must-try restaurants like the superlative French fusion oasis St. Jack, the best Spanish fare in town at Ataula, and some of Beervana's best brews at Breakside. Hotels are, as in many areas, a little harder to come by, though there's a Holiday Inn for the budget conscious and the boutique Northrup Station for folks who don't want to just rent a condo from a traveling Nike employee on Airbnb.

SE Division

Division Street has climbed to the top of the heap of Portland’s restaurant scene, with highbrow fare from Italian hotspot Ava Gene’s and upscale Mexican joint Nuestra Cocina living comfortably with the city’s best slice shop, Scottie’s, plus a pair of dynamo fried chicken spots in the form of upscale Woodsman Tavern and Oregon's best dive bar, Reel ’m Inn.

But simply eating your way up and down Division (which you absolutely should do) isn’t the only reason to actively seek an Airbnb in this hotel dead zone: It’s also walking distance to Hawthorne Boulevard, the paragon of Portland’s hippie-dippie past that represents one of the best shopping districts in town with its combination of earthy and hip boutiques. It’s also extremely near Belmont -- a street that functions as a distillate of the best parts of Hawthorne and Division  -- and stands at the foothills of Mt. Tabor, the east side’s natural crown jewel, a volcanic cinder cone ripe for hiking and taking in the sunset. If you’re staying in SE Portland, this is your home base.

Going somewhere? Check out Thrillist’s other comprehensive Destination Guides to New Orleans, San Diego, Miami, Austin, Vegas, and New York. Keep a lookout for a new travel guide coming soon.

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