I've made every Portland mistake. I stood in a 40-minute Voodoo Doughnut line, pumped my own gas and confused the attendant, and walked through Forest Park in canvas sneakers that became sponges. Learn from me.
This is rule number one. Portlanders do not use umbrellas. The rain here is usually a persistent drizzle, not a downpour, and the wind makes umbrellas useless anyway. Wear a waterproof shell jacket. Columbia, Patagonia, REI brand — anything with sealed seams.
If you walk around Portland with an umbrella, you're broadcasting "I'm from somewhere else" louder than any accent could.
Rainy Portland and sunny Portland are essentially two different destinations. Summer brings 22-30°C temperatures, clear skies, and some of the longest days in the US (sunset after 9PM in June). The city comes alive with outdoor festivals, rooftop bars, and patio dining.
If you have flexibility, go in summer. If you go in winter, embrace the rain — the breweries and bookstores are even cozier.
Portland hit 46°C (116°F) in June 2021. Many older buildings and Airbnbs lack air conditioning. If you're visiting in summer, confirm your accommodation has AC. Heat events are becoming more common.
Voodoo Doughnut is a Portland institution and a tourist magnet. The bacon maple bar is photogenic. The line is 20-40 minutes.
Blue Star Donuts — three blocks away — makes brioche-style doughnuts that are categorically superior. The blueberry bourbon basil doughnut ($4) is the best donut in Portland. No line. Portlanders know this. Now you do too.
Portland's food cart pods aren't a novelty — they're the city's primary food culture. 500+ carts serving cuisine from 60 countries. Most meals: $8-14. The quality competes with sit-down restaurants at half the price.
My top carts:
Screen Door on SE Burnside has the best brunch in Portland. The praline bacon ($4 add-on) is unreal. The Crab Cake Benedict ($19) is a reason to exist.
But: weekend brunch lines are 45-90 minutes. Strategies: go on a weekday, arrive at 8AM, or put your name in and walk to nearby shops. No reservations for brunch.
Stumptown Coffee started in Portland and is now owned by a multinational. The original location on SW 3rd Avenue still serves excellent pour-over ($5). But for truly independent, cutting-edge Portland coffee, try Coava (SE), Heart Coffee (NW), or Upper Left Roasters (NE).
Oregon state law prohibits self-service gas. An attendant pumps your gas for you. Stay in your car, hand over your card, and don't try to touch the pump. There's no extra charge. It's the law, not a premium service.
Every out-of-state visitor learns this the confused way.
The Hop Fastpass card ($5/day, $100/month cap) covers MAX light rail, buses, and the streetcar. The MAX runs from the airport to downtown and covers most tourist areas. It's clean, reliable, and way cheaper than ride-shares.
Buy a Hop card at any MAX station or use contactless payment (credit card tap).
Portland has 350+ miles of bikeways. During rush hour, biking is literally faster than driving for most crosstown trips. BIKETOWN bike-share ($0.10/minute) has stations everywhere. Protected bike lanes separate you from traffic on major routes.
Oregon has no state sales tax. Zero. Clothes, electronics, shoes, books — listed price is final price. If you need to buy anything, buy it in Portland. This saves 6-10% compared to most other states.
Powell's City of Books is amazing. It's also a place where you'll accidentally spend 3 hours and $60. Set a budget before you walk in. Or don't — I won't judge.
The used section has the deals. First editions and rare books are in the Gold Room on the top floor.
The Alberta Arts District holds Last Thursday Art Walk (monthly, May-September, 6-9PM). It's the bigger, livelier, more Portland version of the Pearl District's First Thursday. 60+ open studios, street performers, food vendors. Free.
Don't confuse the two. Both are worth attending, but Last Thursday is the one locals actually get excited about.
Portland has more strip clubs per capita than any US city. Many serve excellent food. Acropolis Steakhouse is a strip club that's genuinely known for its steak ($18 ribeye). This is peak Portland weird. You don't have to go. But knowing it exists is part of understanding the city.
The TV show exaggerated Portland's quirks by about 10%. The artisanal mayonnaise shops, the fixie bike culture, the aggressive recycling — it's all real. Embrace the weirdness. That's the whole point.
Perfect for rainy evenings when you don't want to bar-hop. Spend the last two hours of the day browsing with no time pressure. The cafe inside has decent coffee and a window seat overlooking Burnside Street.
The most photographed waterfall in Oregon (30 minutes east of Portland, 620 feet) requires a timed-entry permit from May through September. $2 per person. Book at recreation.gov up to 2 weeks in advance. Without a permit, you're not getting in during peak season.
Portland doesn't have one big thing. It's not the Space Needle (Seattle) or the Golden Gate (San Francisco). It's a city of small, excellent things — a perfect pour-over, a $12 food cart meal that outperforms a $40 restaurant plate, a bookstore that swallows an afternoon, a forest hike twenty minutes from downtown. For more insights, check out our Portland travel journal. For more insights, check out our complete guide to Portland.
The people who love Portland love it for the accumulation of these small things. Bring a rain jacket, leave the umbrella, and let the city show you why it's worth keeping weird.
