How To Spend A Perfect 48 Hours In Portland

Stoller Family Estate vines and Mt. Hood

Photo Credit: Mike Haverkate

With a thriving culinary scene, nearby wine country, and liberal politics, Portland Oregon isn’t that different from San Francisco. And yet, it’s completely distinct and makes a fun destination for a quick and easy escape. Here’s how to spend 48 perfect hours in Portland. 

Get there: At under two hours of flight time, one can hop on a plane in the afternoon and arrive at the famed Multnomah Whiskey Library for happy hour by 5 p.m. 

The lobby at The Duniway

Photo Credit: The Duniway

Stay: The Duniway is a stylish boutique hotel in the heart of downtown Portland. The chic lobby feels like a living room, and its bar is a popular hot spot among locals. The hotel is named after Abigail Scott Duniway, a pioneer and women’s rights activist. Her spirit is channeled throughout: rooms are stocked with books written by other Portland-based trailblazers and the Duniway family crest is on the room keys.

A modern bathroom

Photo Credit: The Duniway

With a neutral color palette, velvet couches, and dark wood furniture, the rooms are cozy and inviting, but luxurious. Decorative accents—geometric tiles in the shower, rose-print wallpaper in the closet, moose artwork on the walls—keep things playful and add a touch of whimsy. The Duniway is within walking distance to the famed bookstore, Powell’s, hip cafes like Heart Roasters, and boutiques such as Wildfang.

A 28-day aged four-pound steak

Photo Credit: Mark Mediana

Eat: Chef Chris Cosentino is behind the Duniway’s wildly popular ground-floor restaurant, Jackrabbit. With pig’s head, fried rabbit, and housemade pasta, the menu reflects his whole-animal and Italian background. If vegetables are more up your alley, head to Tusk, a restaurant that serves Middle Eastern cuisine made with local, seasonal ingredients in a happening environment. From the creamy hummus to the balanced salads to the fragrant saffron rice, everything on the menu is delicious.

A picnic spread at Stoller

Photo Credit: Carolyn Wells

Do: Oregan is known for its Pinot Noir, and you’ll find plenty of it at Stoller Family Estate. The winery, which is a 40-minute drive from The Duniway in the Dundee Hills AVA, is a family-friendly destination with plenty of room to picnic. Warning: the wines are so good that you might have to check your bag on the return flight home.

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