So, you’re planning a trip to Portland, Oregon? Excellent choice! After living here, I’m excited to share my insider tips and recommendations to help you experience the best of this unique city. Forget the usual tourist traps; this is a local’s perspective on what to see, do, and eat in Portland. Consider this your personalized roadmap to discovering the true essence of the City of Roses.
Getting to Portland: Your Travel Options
Flying into PDX: Portland International Airport
Portland International Airport (PDX) is well-connected, with service from all major US airlines, including United, Delta, Alaska, American, and Southwest. However, flights from the East Coast can be pricey. Consider using points and miles, especially Alaska flights, and transferring points to British Airways for potential savings.
PDX isn’t just a transport hub, it’s an experience. If you have a Priority Pass (often obtained through credit cards like Chase), check out Capers Cafe Le Bar and Westward Whiskey for a discounted bite or drink.
Road Trip or Rail: Portland by Car or Train
Portland is easily accessible from Seattle by car or Amtrak train (both around 3 hours). However, I advise against combining both cities into a single trip unless you have a week or more. Each city boasts incredible day trip options (Mt. Rainier, the Olympic Peninsula, and the San Juan Islands from Seattle; the Columbia River Gorge, Mt. Hood and the Oregon Coast from Portland), warranting a dedicated 5-7 day trip each.
Navigating the City: Getting Around Portland
While Portland offers public transportation, I recommend renting a car for optimal exploration. The light rail and streetcar systems can be limiting, especially if you want to experience all four quadrants of the city and beyond. Ride-sharing services are readily available, but a car provides the flexibility to explore outside of the city center.
Traffic in Portland is generally manageable, and parking is usually easy to find. Expect travel times to be relatively short, often just 10-15 minutes, regardless of your destination within the city.
The Best Time to Visit: Portland’s Weather and Seasons
Portland has two primary weather modes: gray and rainy, or stunningly beautiful. Climate patterns have become less predictable due to global warming, but the rainy season typically begins in November and can last until late June. For the best chance of dry weather, plan your visit for July, August, or September. You’ll enjoy blue skies and moderate temperatures. While it can get hot, the humidity is generally low, making it comfortable.
Be prepared for rapid weather changes, regardless of when you visit. Rain can be intermittent, and cloudy mornings can transform into sunny afternoons. Pack a rain jacket year-round to stay prepared and enjoy outdoor activities regardless of the weather.
Where to Stay: Portland’s Neighborhoods and Hotels
Portland is divided into five main quadrants: Northwest, Southwest, Northeast, Southeast, and North. The Willamette River separates the east and west sides, each with its own distinct personality.
The east side is more “Portlandia,” with eclectic shops, independent businesses, street art, and a residential feel. The west side, home to downtown, has a more urban vibe with historic architecture, including red-brick warehouse buildings repurposed into shops and restaurants.
While many recommend Airbnbs on the east side for an authentic experience, I suggest considering hotels on the west side. Downtown is walkable, and you can easily access the east side and surrounding areas by car.
Here are a few hotel recommendations:
Hotels You Can Book with Points
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The Porter Portland (Curio Collection by Hilton): Comfortable rooms, streamlined decor, and city views. Bookable with Hilton Honors points.
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The Hi-Lo Hotel (Autograph Collection by Marriott): Beautiful spaces, a central location, and a Northwest-inspired restaurant. Bookable with Marriott Bonvoy points.
Hotels Without Points Options
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The Woodlark: Home to Good Coffee and Abigail Hall cocktail bar.
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The Hoxton: A trendy hotel with Tope, a rooftop taco bar, and a speakeasy.
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Ace Hotel: Ideally located in downtown, close to the Pearl District and Pioneer Courthouse Square.
Things to Do: Unveiling Portland’s Attractions
Nature Activities: Embrace the Outdoors
- International Rose Test Garden: Explore over 10,000 roses in bloom during the summer. Enjoy the views from the lawn.
- Forest Park: Hike through 80 miles of trails in one of the largest urban forests in the US.
- Mt. Tabor: Visit an extinct volcano with a public park, hiking trails, and 360-degree views.
- Cathedral Park: Admire the St. Johns Bridge from below in this park along the Willamette River.
Urban Activities: Explore the City’s Culture
- Alberta Arts District: Browse eclectic shops, independent businesses, and street art in this Northeast neighborhood.
- Shop on SE Hawthorne and SE Division: Discover unique boutiques, cafes, and restaurants along these two thoroughfares.
- Powell’s City of Books: Explore the world’s largest used and new bookstore, spanning an entire city block.
Views: See Portland from Above
- Portland Aerial Tram: Ride between the South Waterfront and Oregon Health & Science University campus for breathtaking city views.
- Portland Saturday Market: Stroll through the market along the Willamette River and enjoy the riverfront views.
- Pittock Mansion: Visit this historic house museum for stunning skyline views.
Day Trips: Adventures Beyond the City
West of Portland
- Columbia River Gorge: Visit Multnomah Falls or hike Angels Rest. Explore Hood River, a town with breweries and mountain views.
- Mt. Hood: Hike the Tom, Dick and Harry Mountain Trail or visit Timberline Lodge.
East of Portland
- Willamette Valley (Oregon Wine Country): Visit wineries around Dundee and McMinnville.
- Cannon Beach/Oregon Coast: Explore rock formations and tidepools. Stop at Ecola State Park for incredible views.
Where to Eat: A Local’s Guide to Portland’s Culinary Scene
Sit-Down – Reservations Recommended
- Ava Gene’s: A modern Italian restaurant on SE Division.
- Tusk: A Mediterranean restaurant that serves shareable small plates.
- Kachka: Modern Russian cuisine with dumplings (pelmeni).
Sit-Down – Mostly Walk-In
- Tope: Rooftop taco bar at The Hoxton with sunset views.
- Afuri Izakaya: Japanese ramen chain with its first location outside Japan.
- Tasty & Alder: Brunch spot.
Casual Dining
- Proud Mary: Australian cafe with healthy dishes.
- Lardo/Bunk Sandwiches: Sandwich chains.
- Sizzle Pie: Pizza.
Dessert
- Blue Star Donuts: Artisanal doughnuts.
- Cloud City Ice Cream: Ice cream with unique flavors.
Where to Drink: Portland’s Cocktail, Wine, Beer, and Coffee Scene
Cocktails
- Hale Pele: Tiki bar with drinks and effects.
- Abigail Hall: Cocktail bar in The Woodlark hotel.
- Pepe Le Moko: Cocktail bar inside the Ace Hotel.
- Vault Cocktail Lounge: Chill bar with cocktails in the Pearl District.
- Basement Bar: Speakeasy in the basement of The Hoxton.
Wine and Beer
- Oui! Wine Bar + Restaurant at the Southeast Wine Collective: Wines and food.
- Breweries: Explore the city’s brewery scene.
Coffee
- Good Coffee: Seasonal latte flavors.
- Coava Coffee: Roasts its own beans.
- Upper Left Roasters: Coffee, macadamia milk, and toasts.
Still On My List: More Portland Adventures
- Multnomah Whiskey Library: A collection of distilled spirits.
- Portland Japanese Garden: Japanese garden with tea ceremony presentations.
- Woodblock Chocolate Manufactory: Watch chocolate being made while dining in a chocolate cafe.
- Swiss Hibiscus: A restaurant with Swiss cuisine.
I hope this local guide helps you plan your trip to Portland, Oregon! Let me know if you have any other questions.
