With its vibrant downtown and eclectic neighborhoods, Portland promises an abundance of activities for almost any traveler. Foodies flock to the microbreweries, artisanal eateries, and independent coffee shops. Shoppers will find plenty of design-savvy boutiques stocked with everything from design goodies to edgy fashions, classic books to outdoor apparel. And nature lovers will appreciate the hills and Douglas firs, not to mention day trips to Mt. Hood (don’t forget to pack your flannel) and nearby coastal spots like the seaside town of Astoria.
Top-Tier Dining
You'll want to eat everything in Portland—so pace yourself and plan meals accordingly. In southeast Portland, the critically acclaimed Italian spot Ava Gene’s is best enjoyed at the small counter, where you can watch the kitchen line work their magic on the fresh pastas of the day plus hearty meats like ribeye with squash, hazelnuts, and a pecorino called Fiore Sardo.
In the Mt. Tabor neighborhood, the new Coquine from chef Katy Millard is a narrow, accessible-wine-and-sandwich spot by day. Do yourself a favor and order the porchetta on ciabatta with cabbage, basil, mint, and lemon; sip a crisp white wine; and indulge in the perfect chocolate-chip cookie. In the evenings, the menu features dishes like black cod with fresh coco bianco, sweet pepper sofrito, and pancetta.
Downtown, the venerable Clyde Commons (part of the hipster paradise at the Ace Hotel), is now helmed by chef Carlo Lamagna and is the place for fried-chicken roulade, been salad, espelette biscuits, and gravy. Afterwards, digest with a drink like the Sophomore Slump (rye, Italian vermouth, Averna, bitters, and orange peel), slung by the capable Jeffrey Morganthaler. If you still have room, Blue Star Donuts (with new outposts in Japan and Los Angeles) are made from a fluffy brioche recipe and include a decadent, Instagram-worthy options like blueberry with bourbon and basil and Valrhona chocolate crunch, lovingly (and dangerously) filled with vanilla custard.
Behind chef Trent Pierce’s BT Oyster Bar (stocked with fresh Washington State oysters) is a second secret spot, Roe. With only 30 seats, it offers a rotating tasting menu that's keenly invested in fresh fish. Elsewhere, from her open kitchen at Lincoln, James Beard Award-nominated chef Jenn Louis (who also helms the awesome Sunshine Tavern) serves straightforward, unpretentious meats and pastas such as rigatoni with chicken ragu and parsley.
The spacious Red Star Tavern is smart for small plates like the "tavern toast" (olive relish and goat cheese) and a microbrew. Really hungry? Stay for chef Kyle Rourke’s smoked wagyu brisket. On the carnivore front, the old-school steakhouse (in the vein of Brooklyn’s Peter Luger) is Ringside Steakhouse, which takes honors for their dry-aged steaks glazed with butter and served by sharp, tuxedoed waiters. Meanwhile, under-the-radar Davenport scores points for its seasonally-changing simplicity and refined, fresh ingredients and reasonably priced insider wine list to boot.
Microbews Cocktails Galore
Of course, the microbrews are vast in Portland; in fact, the city currently holds record for most per capita. For a unique twist, head to Base Camp Brewing Company and try malty S’more Stout with a roasted marshmallow perched on top. Zip over to Mississippi Street for a pint at Storm Breaker and later, across the street, Mississippi Marketplace hosts food trucks that serve vegan-friendly rice bowls and Korean tacos.
There’s a nascent local cider movement that is producing surprisingly complex beverages. For great tastings, make stops at Reverend Nat’s Hard Cider, Portland Cider House, Wandering Aengus and Bushwhacker to experience the new wave of cider yourself.
The Space Age-styled Departures (on the rooftop of The Nines) offers stellar panoramic views as you sip on sake and chow on Top Chef runner-up Gregory Gourdet’s Asian fusion plates. A few blocks away, the handsome Multnomah Whiskey Library is Old World chic with dim lighting and walls upon walls of whiskey. Small, intimate Angel Face, with lovely pink-hued wallpaper, is a perfect spot to nab cheese and charcuterie boards and steak tartare, not to mention polished handcrafted cocktails. There's no cocktial list, only whatever your heart desires, shaken to order. The hip Sweet Hereafter serves their namesake drink with vodka, bourbon, lemon, and iced tea in a mason jar. Drink up!
Chic Boutiques
Since 2005, the long-standing, popular design shop Canoe (which recently relocated a few blocks away) has stocked their own exclusives (Eena Canvas bags and Mazma Ceramics tumblers), plus Oregon-designed products alongside delicate Noguchi lanterns and Heath Ceramics. The cooler-than-thou Frances May is an indie, unisex clothing stop for labels like Acne Studios, Rachel Comey, Correll Correll, and Saturdays tees for the gents. The outdoor outfitter Poler Stuff sells stylish cold-to-warm weather gear, from stocking caps to tents to backpacks. Colorful Woonwinkel hawks brightly covered blankets and textiles, tabletop items, and local goods. For an easy, compact shopping experience, charming Union Way is a narrow shop-lined alleyway including Steven Alan, denim from Self Edge, sturdy boots from Danner, niche grooming products made by Ursa Major and Fig + Yarrow at Spruce Apothecary, and a colorful candy shop called Quin.
One-of-a-Kind Souvenirs
Remember, Portland puts the "l" in local, so don’t leave town without buying some unique and affordable souvenirs. Using coconut and essential oils, OLO Fragrances channel the Pacific Northwest in scents like Cedar Rose and Wyeth, a mix of rain and pine trees. Chocoholics should head to the family-run Woodblock Chocolate for two reasons: the fantastic packaging and the quality of their dark varietals, including 70% Toasted Sesame, Salt and Nibs, and the Madagascar.
The beloved Jacobson Salt Co. sources locally from the chilly waters near Netarts Bay, and varieties like Flaking Finishing Sea Salt and Pink Himalayan. Portland’s Apothecary turns out a variety of handmade soaps like the divine Forest edition, made with cedarwood and vetiver.
Wolf’s Apothecary’s hand-poured soy and beeswax Evergreen candle gives you the forest without stepping foot among the green. Besides thousands of books, the legendary indie Powell’s Books carries great tote bags bearing the store’s name and a funky variety of Sock It To Me Socks. In a well-known coffee town, the caffeinated set will love the authentic bags of beans from Ristretto Roasters. Lastly, nab some goodies at Smith Tea, where you'll find a variety of black and white teas and herbal infusions like peppermint leaves and a blend called Meadow using chamomile, rooibos, rose petals, and linden flowers.
Easy Side Trips
Renting a car gives you freedom to explore the various regions near Portland, from Willamette Valley wineries to the smaller artist haven of Eugene. Take a trip to the neighboring Hood River; nearby, you'll find various trails to hike and expand your lungs in the fresh mountain air. The early bird catches the worm, so hike early and then stop by Double Mountain Brewery Taproom for a brick-oven, New York-style pizza washed down with a lager. Afterwards, head to the microbrewery Pfiem for views of the Columbia and White Salmon rivers. If there’s a chill, nab a seat around the outdoor patio complete with a fire pit.
Where to Stay
With just 84 rooms, The River Place Hotel sits on the peaceful Willamette River. In the mornings, watch the early kayakers, read the paper by the warm fireplace, and sip the local Caffe Vita brew. At night, you'll find complimentary beers from the Widmer Brothers. Need some exercise? The hotel provides a fantastic jogging map with various routes ranging from 3–7 miles. To end your day, grill complimentary s'mores’ between sips of warming Pendleton whiskey as you head to your comfortable bed topped with another local delight, a Pendleton Woolen Mills Los Ojos Sham.