48 Hours in Portland: The Ultimate Itinerary

Portland sign next to a skyscraper in downtown Portland

TripSavvy / Chris VR

Visitors have been flocking to Portland in recent years, and it’s easy to see why. The city is surrounded by natural beauty, including forests, mountains, rivers, gardens, and unique urban parks. Plus, it’s home to one of the hottest culinary scenes in the country (everything from wallet-friendly food trucks to swanky fine dining restaurants), and it's a destination for shopping, bookstore browsing, urban hiking, and taking in a show. PDX is approachable too—the locals are nice, and the city is small enough that travelers can get a good sense of it in just a few days. Follow this itinerary for the perfect weekend in this Pacific Northwest gem.

A large garden of roses surrounded by tall green pine trees
TripSavvy / Ana Alarcon

Day 1: Morning

10 a.m.: Exploring farmers markets is one of the best ways to get to know a city. And while Portland has dozens of open-air markets overflowing with Pacific Northwest bounty, the P.S.U. Portland Farmer’s Market is something special, often lauded as one of the best in the country. Open year-round on Saturday mornings until 2 p.m., it’s the perfect place to kick off your day. Start with a cup of coffee from the Nossa Familia stand and fresh and healthy-ish Mexican breakfast dishes from Verde Cocina (think handmade tortillas topped with eggs, chorizo, mounds of grilled PNW veggies, and mole sauce). Listen to the live music and do some people-watching. Before you leave, pick up some edible souvenirs to bring home (if you can make them last long), like local hazelnuts, smoked salmon, chocolate, lavender, and Willamette Valley wines.

11 a.m.: Continue exploring Portland’s west side with a visit to these two gorgeous gardens. They’re next to each other in Washington Park, just a few minutes from downtown. Start at the Portland Japanese Garden ($19 for adults), and stroll 12 gorgeous, tranquil acres, including a Natural Garden, Bonsai Terrace, Strolling Pond Garden, and Tea House. And don’t miss the modern, new Cultural Village to immerse yourself in Japanese art and cultural activities.

Once you’ve made a leisurely loop, head down the hill and cross the parking lot towards the International Rose Test Garden, which was founded as a way to prevent rose varieties from being destroyed in bombings during World War I. The moment you clamor down the stone steps and the garden comes into view, you’ll understand why Portland is called the City of Roses. The garden has more than 10,000 rose bushes and 650 rose varieties, which perfume the air and create an explosion of color (pure white, sunny yellow, saturated red, and pinks ranging from pale to hot). There are also fantastic views of downtown Portland and Mt. Hood. Best yet, the garden is free.

Day 1: Afternoon

1:30 p.m.: What…your city doesn’t have a whimsical Modern Pastry Luncheonette with an eclectic mix of refined French bistro fare, snacks, and drinks for fika (the Swedish version of a coffee break), and world-class pastries? Go to Måurice, which was named one of the top 10 restaurants in the country by Bon Appétit magazine when the restaurant opened in 2014, for a light lunch of salad, soup, oysters, or lefse with gravlax. Or sit at the bar sipping a glass of wine of one of dozens of vermouth. Whatever you order, don’t leave without indulging in Maurice’s pastries and sweets, including its famous Lemon Soufflé Pudding Cake or Black Pepper Cheesecake.

3 p.m.: Powell’s City of Books is not just a Portland institution, it’s also the biggest new and used bookshop in the world. Plus, its location on West Burnside Street, the street that bisects the city, makes it the perfect place to start exploring downtown and The Pearl. Shop national retailers including Anthropologie, REI, Madewell, Sur la Table, Shinola, Filson, and West Elm. But don’t miss local shops including Cielo Home, Lucy sportswear, Popina swimwear, Oblation Papers & Press, Canoe home goods, Frances May women’s boutique, and Oregon’s iconic Pendleton. Also not to be missed is Tender Loving Empire, which stocks jewelry, clothes, art, and other handmade goods from local artists perfect for gifts or souvenirs. 

Day 1: Evening

8 p.m.: Head to Tope, the new hipster-chic Hoxton hotel’s rooftop restaurant to tuck into Mexican taqueria-inspired eats with killer views of Portland. Start with queso fundido, salmon ceviche, or the chicharrones and avocado salsa. To drink, order a classic margarita or michelada, or go for one of Tope’s tasty mezcal cocktails like the Carrot on My Wayward Son, made with Bahnez mezcal, carrot, sweet potato, lime, mole bitters, and egg white. Then, mix and match tacos stuffed with lengua, rockfish, spicy lamb sausage, roasted cauliflower, or beef cheek in adobo. 

10:30 p.m.: More than 1,500 whiskies accessed by rolling copper ladders line the walls at The Multnomah Whiskey Library, a gorgeous drinks den downtown. Settle into one of the leather club chairs or couches and peruse the extensive spirits menu. Don’t worry if you’re not a whiskey fan: the menu has pages of other spirit options and classic cocktails like the Old Cuban, a rum drink with fresh lime and mint that gets topped off with a Champagne float that MWL does perfectly. If there’s a wait for a table (there usually is), get your name added to the list and have a quick drink downstairs at emerald-colored Green Room.

View of downtown from Mt Tabor Park
TripSavvy / Ana Alarcon

Day 2: Morning

10:30 a.m.: The cult-fave neighborhood spot Pip's Original on NE Freemont makes just two things—doughnuts and chai—and they make them perfectly. Portland might be best known for a colorful, over-the-top Voodoo Doughnuts topped with sugary cereal, bacon strips, and purple Kool-Aid powder. But if you’re going for taste over novelty, these are Portland’s best bites of fried dough.  

Expect a line when you roll up to Pip’s on NE Freemont. Don’t worry, it moves at a steady clip, and it’s worth the wait. The simple mini doughnuts are made to order, and come as four, six, eight, or a dozen. Once the piping-hot rounds emerge from the fryer, they’re topped a dab of cinnamon sugar, Nutella, or seasonal flavors like Marionberry-lavender in summertime. But it’s hard to do any better than the standard drizzle of honey and sprinkling of sea salt. 

11:30 a.m.: It’s not everyday that you get to hike a volcano smack dab in the middle of a city. Don’t worry about the threat of hot lava at Mount Tabor Park on SE 60th Avenue and Salmon Street: the volcanic cinder cone has been dormant for a few hundred thousand years. Now it’s one of Portland’s best-loved parks, with acres of options for burning off some calories, including hiking and running trails, plus tennis, basketball, and volleyball courts. Towards the east, you’ve got fantastic views of Mt. Hood and other Cascade Range mountains. At the top of Tabor, look west for gorgeous views of downtown Portland, its bridges, and the verdant West Hills.

Day 2: Afternoon

12:30 p.m.: You can’t leave Portland without eating from one of its famous food carts. So on your way out of Mt. Tabor, swing by the food cart “pod” on nearby SE Belmont and 43rd, or drive a few minutes more to the ever-popular pod of carts on SE Hawthorne and 12th. The pods are great if you can’t decide what you’re in the mood for, or if you can’t agree with your travel partner. At the “Bites on Belmont” pod, you’ll find everything from coffee and beer carts to Mexican breakfast burritos and stuffed poblano peppers, Brazilian feijoada, and moqueca, and fish from the waters of the northern Pacific. Over at “Cartopia” on Hawthorne, you can sample Latin roasted chicken, French crepes, Mexican tacos and sopes, Italian wood-fired pizzas, and upscale American PB&Js made with creative ingredients.

5 p.m.: Kick off your weekend with Portland’s most famous dish: Pok Pok’s Vietnamese Fish Sauce Wings. The restaurant has a few outposts, but none have the scrappy soul of the original location on Southeast Division. Today Chef Andy Ricker has racked up a couple James Beard Foundation Awards. But back in 2005 when he opened the restaurant, he lived in the house, cooked in the commercial kitchen below, and sold his Vietnamese and Thai-inspired BBQ dishes through a takeout window. Stop by Pok Pok for some of his highly-addictive wings and a refreshing cocktail made with housemade drinking vinegars, or grab a picnic table outside its sister bar across the street, Whiskey Soda Lounge. Share a plate of wings so you have room for later: you’ll need it.

Day 2: Evening

6:30 p.m.: Head left out of Pok Pok and walk a couple blocks for boldly-flavored Indian street food at Bollywood Theater, or turn right to tuck into plates of handmade pasta and outstanding vegetable dishes at the more upscale Roman-Italian restaurant Ava Gene’s. Check out the shops, bars, and restaurants lining this trendy stretch of Division, and grab some of the city’s best sweets. Go to Salt & Straw for creative ice creams, or old fashioned, grandma-approved pie at Lauretta Jean’s.

8 p.m.: Continue your tour of Southeast Portland by hearing some live music at one a few perfectly Portland venues a short drive away. Doug Fir Lounge at the Jupiter Hotel on East Burnside is a local institution: you’ll feel like you’re in a friend’s basement as you rock out to a show in the mid century-inspired lounge’s lower level. Or head to Revolution Hall on SE Stark, where you can live out a teenager fantasy as you listen to bluegrass, indie rock, a lively podcast taping, sing-along, or burlesque show in the 700-seat auditorium of this former high school.