The Perfect Weekend in Portland, Oregon

Photo: © Brian Jannsen / Alamy

Portland has warm, dry summers and soggy, gray winters, meaning depending on the season, you’ll want to change your activities to have the ideal weekend: a hike and visit to gardens in the summer, or a visit to an outdoor hot tub or the country’s largest bookstore on a rainy day. No matter what the weather is, plan on eating—and eating, and eating—plus drinking plenty of locally made beer, wine, and coffee. With several James Beard-nominated chefs, no sales tax on food or booze, and tons of organic produce at its disposal, Portland is a foodie destination that caterers to vegans, bacon-lovers, and everyone in between. Here’s how to get the most of your time in town.

Where to Stay

The Nines, a luxury hotel located downtown, has thoroughly modern furnishings in a historic, 1909 building. There’s a 419-piece art collection onsite, and the property offers bi-weekly guided art tours. The hotel’s rooftop restaurant, Departure, has great views and is run by recent Top Chef runner-up Gregory Gourdet.

Where to Eat

For breakfast, Pine State Biscuits serves the Reggie, the best fried chicken on a biscuit (plus bacon) outside of North Carolina, or you can head to Voodoo Doughnuts, serving maple bacon bars and Cap N’ Crunch donuts around the clock (because it’s Portland, they also offer vegan varieties). For dinner, head to Southeast Division Street, a several-block stretch made up almost entirely of restaurants.

Snag a spot at the counter at rustic Italian Ava Gene’s, co-owned by the founder of Stumptown Coffee whose chef cooked for Momofuku and Blue Hill. Or skip the hours-long wait at Pok Pok, James Beard Award-winner Andy Ricker’s Thai street food shack, and try his less-jammed, just-as-delicious restaurants that are a few doors down, Sen Yai or Whiskey Soda Lounge. Finish your Division Street foodfest with a scoop from Salt & Straw, with one-of-a-kind ice cream flavors like pear and blue cheese, or balsamic strawberry and black pepper.

Where to Drink

The Multnomah Whiskey Library looks like a library—leather chairs, desk lamps, sliding ladders and all—but instead of books, it stocks 1,500 bottles (if you’re easily overwhelmed, check out the curated tasting menu). If you’re more into wine, sip at the unpretentious Southeast Wine Collective for affordable flights of local Pinot Noir, Pinot Gris, or rarer wines like Chenin Blanc and Oregon Nouveau. For those who prefer beer, there are more than 50 craft breweries in town, but a favorite is Hopworks BikeBar, powered with renewable energy that you can contribute to by pedaling a stationary bike, usually after a few pints.

What to Do

Work off those decadent meals, especially if the weather’s nice, with a hike in the Columbia Gorge, just a 45-minute drive from the city. The 2.6-mile Horsetail Falls’ trailhead starts at a waterfall, and the trail passes behind Ponytail Falls, so you’re in a lava-flow cavern behind another waterfall.

Or stay in town for a hike in the city’s Forest Park, one of the largest natural areas in any city in the U.S., filled with fiddlehead ferns. Then stroll around the nearby International Rose Test Garden, sniffing blooms that are being developed and evaluated for scent and color, and can’t be seen anywhere else in the world.

Browse the Rare Room at Powell’s City of Books, the country’s largest independent bookstore, remodeled last year. Or spend the afternoon at McMenamin’s Kennedy School, a quirky, refurbished 1915 elementary school: you can catch a movie, soak in the heated outdoor saltwater pool that feels like an oasis, or have a cocktail and smoke a cigar in what was once the principal’s office.

Sarah Z. Wexler is on the Oregon beat for Travel + Leisure. Based in Portland, you can follow her on Twitter at @SarahZWexler.

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