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.