Portland, Oregon, known for its alternative spirit, has become one of America’s top food cities with excellent restaurants helmed by creative chefs, a food cart culture with hundreds of culinary vendors offering multi-ethnic casual dining, numerous high-end coffee roasters and easy access to world-class wineries in the Willamette Valley. In addition, Portland is one of America’s most scenic cities with snow-covered mountains towering in the background and easy access to stunning vistas and waterfalls of the Columbia River Gorge.
For this weekend, we recommend the charming Sentinel Hotel, a luxury downtown hotel located in a building dating from 1909. The character-filled hotel features a double-height lobby with an intricate ceiling, period styling and an extensive collection of black & white photographs of iconic figures adorning the hallways. We recommend their Terrace Suites that feature cozy outdoor terrace with a fire pit and sweeping city views. The suites also have access to a comfortable private lounge that is stocked with drinks and snacks throughout the day.
Sentinel Hotel // 614 SW 11th Avenue // website
Portland is known for its gourmet food cart culture where you will find clusters (known as “pods”) of food carts throughout the city. The Alder Street Food Court Pod, just down the street from the Sentinel Hotel and filling an entire city block, is the largest downtown collection of food carts. Here you will find some of the best food carts in Portland, including Nong’s Khao Man Gai, which specializes in a single Thai dish called Khao Man Gai that consists of broth-poached chicken over rice and served with a sweet garlic-laced chili and fermented soybean sauce; The Dump Truck specializing in savory dumplings for both vegetarians and meat lovers; the Whole Bowl serving healthy bowls of rice, beans, avocado, salsa and cheese and The Frying Scotsman, which is highly regarded for its fish and chips.
Adler Street Food Court Pod // S.W. 10th Ave. & Alder St. // website
After sampling the offerings at the Alder Street Food Court Pod, head north to the Pearl District, a former industrial area with converted warehouses and cobblestone streets that has become one of Portland’s trendiest neighborhoods. The Pearl District has an eclectic mix of breweries, galleries, boutiques and restaurants. Your first stop should be Powell’s Books, where you can get lost in the largest independent bookstore in the United States covering an entire city block. Also check out Filson, located in the historic Confectionary Building, famous for their rugged outdoor clothing and bags since 1897.
Powell’s Books // 1005 W Burnside St. // http://website
Filson // 526 NW 13th Ave. // website
After exploring the Pearl District, head to the serene Japanese Garden located in Washington Park, a 160-acre park on the slopes of the West Hills overlooking Portland. The six-acre Japanese Garden is one of the most beautiful and peaceful spots in Portland and features a strolling garden with a pond filled with dozens of koi, arched bridges and a waterfall, a meditative tea garden with tea house and a traditional raked stone garden. The Japanese Garden is a magical place that will make you feel as if you have been transported to a traditional garden in Kyoto.
Portland Japanese Garden // 611 SW Kingston Avenue // website
Also located in Washington Park is the International Rose Test Garden, with over 500 varieties of roses and botanicals. The Rose Garden is spectacular when the roses are in full bloom.
International Rose Test Garden // 850 SW Rose Garden Way // website
For dinner, we recommend Castagna, one of the top restaurants in Oregon. The restaurant is helmed by Justin Woodward, who was nominated for James Beard’s Rising Star Chef award in 2013 and Best Chef Northwest award in 2015 and 2016. Castagna offers a 19-course tasting menu (as well as a smaller 9-course tasting menu) of seafood and vegetable-forward small plates. Some recent standout dishes included a slice of rich foie gras with venus grapes, a ceramic cup filled with snap peas served with goat butter and anise hyssop, a simple dish comprised of slices of albacore and a mix of Japanese and Spanish peppers and a creative vanilla “sundae” with dehydrated black olives and fresh raspberries.
Castagna // 1752 SE Hawthorne Boulevard // website
Portland residents love their brunch on the weekends and you will find one of Portland’s best brunches at Imperial, located in the Hotel Lucia. Some brunch favorites from a recent visit included a homemade remake of the classic “Poptart”; an exceptional pastrami hash; grilled grapefruit with pesto sugar and a smoked-tomato juice Bloody Mary.
Imperial // 410 SW Broadway // website
For today, there is no better way to experience the beauty of the Portland area than a private guided bike trip to the Columbia River Gorge, only 45 minutes from downtown Portland. The Columbia River Gorge is the nation’s largest national scenic area and one of the most beautiful places in Oregon. Your guide from Pedal Bike Tours will lead you on an easy 9-mile ride along the historic Columbia River Highway where you will stop every mile or so for a short hike to up to six spectacular waterfalls, including Multnomah Falls, Horsetail Falls and Bridal Veil Falls. Along the way you may even spot some of the native birds of prey, such as osprey and bald eagles.
Pedal Bike Tours // 133 S.W. 2nd Avenue // website
There are a number of spectacular spots for a picnic lunch at the Gorge so we recommend that you pick up food for picnic lunch in advance at one of Portland’s many gourmet markets.
Before returning to Portland, your guide will take you up the scenic road to the top of the Gorge, stopping at Crown Point for spectacular views over the entire Columbia River Gorge.
After a full day of biking and hiking, there is nothing more satisfying than a delicious ice cream served in a freshly made waffle cone from Salt & Straw, Portland's best ice cream shop. Here you will find very creative (and delicious) ice cream flavors, including Sea Salt with Caramel Ribbon; Strawberry Honey Balsamic with Cracked Pepper; Almond Brittle with Salted Ganache; Pear and Blue Cheese or one of their seasonal choices like Caramel Corn on the Cob.
Salt & Straw // 3345 SE Division St. // website
For an exceptional seafood dinner, head to Roe, Portland’s best seafood restaurant. Currently located at the back of a casual oyster bar (though they are looking to move to new space in late 2016), this tiny 30-seat restaurant feels like a cross between a supper club and a speakeasy. Chefs Trent Pierce and Patrick Schultz offer a four-course menu and a seven-course tasting menu that consists almost exclusively of seafood dishes. The chefs highlight the freshness and quality of the seafood by employing sous vide and other gentle cooking techniques. Recent standout dishes included a heavenly Hawaiian butterfish showered with shaved frozen foie gras and truffled soy ponzu, a meltingly delicious gin-cured salmon cooked sous vide with finger lime, marigold and tonic crema and, for dessert, peaches served on a raspberry-soaked genoise with vanilla ice cream, white chocolate feuilletine and raspberry emulsion.
Roe // 3113 SE Division Street // website
For an after-dinner drink, we love Pepe le Moko, a small, dimly lit (frankly, dark) basement speakeasy, located below Clyde Common in the Ace Hotel, that offers creative takes on classic cocktails and small bites, including freshly shucked oysters served on a bed of shaved ice. We loved their version of an El Diablo, a Trader Vic drink from the 1940’s, made with tequila (we substituted mescal for a smokey flavor), creme de cassis, ginger beer and fresh lime juice.
Pepe le Moko // 407 S.W. 10th Avenue // website
Portland is known for its coffee culture and is home to numerous excellent coffee roasters and craft coffee shops, including the original Stumptown Coffee Roasters. Start your morning with a perfectly brewed cup of coffee from Stumptown Coffee Roasters or, another local favorite, Heart, which lightly roasts its own beans to prepare exceptional drip coffees and espresso drinks. If you feel like a short bike ride, head over to Trailhead Coffee Roasters for an excellent cup of coffee made with coffee beans roasted on premises.
Stumptown // 1026 S.W. Stark Street (multiple locations) // website
Heart // 537 S.W. 12th Avenue (multiple locations) // website
Trailhead Coffee Roasters // 118 NE Martin Luther King Blvd. // website
If you want something sweet with your coffee, stop by Portland’s famous Voodoo Doughnuts, a funky doughnut shop known for their colorful and unusual doughnuts, including their famous bacon-topped maple bar, breakfast cereal-topped doughnuts and an occasional slightly risqué doughnut. While Voodoo Doughnuts is worth visiting for the novelty of their creations, don't expect a transcendental culinary experience.
Voodoo Doughnuts // 22 S.W. 3rd Avenue // website
Just south of Portland is the Willamette Valley, an area which produces world-class Pinot Noir and Chardonnay wines. Although the larger wineries generally have tasting rooms (and sometimes tours) open to the public, many of Oregon’s best wines are crafted by small boutique producers that are only open by appointment and, often, only accessible to wine insiders. We highly recommend booking a private full-day tour with Winemaker Tours, a tour company operated by wine-insiders Jim and Amy Esper, which offers private bespoke tours tailored to your interests. Jim and Amy are able to use their vast connections to visit wineries not generally open to the public and arrange tastings directly with the winemakers.
Winemaker Tours // website
Your day may include visits to Beaux Frères, a winery founded in 1987 by Michael Etzel and famed wine critic Robert Parker, which produces exceptional world-class Pinot Noir wines; Anderson Family Vineyard, a winery that produces fabulous Pinot Noir and Chardonnay wines handcrafted by veteran winemaker Cliff Anderson and Carabella Vineyard, a winery owned by winemaker/geologist Mike Hallock, which produces limited production bottling of Pinot Gris, Chardonnay and Pinot Noir.
Beaux Freres // 15155 NE North Valley Rd. Newberg, OR // website
Anderson Family Vineyard // 20120 NE Harring Lane, Newberg, OR // website
Carabella Vineyard // website
One of the best Willamette Valley restaurants is Jory, located at The Allison Inn & Spa. The restaurant, helmed by Chef Sunny Jin who worked under Thomas Keller and spent time at El Bulli, features an open kitchen and offers terrace seating that is perfect for warm summer days. The brunch menu emphasizes seasonal, farm-to-table dishes, including a grilled King salmon BLT, an exceptional “pinot” burger with beecher’s cheese and a delicious “porkstami” hash. The restaurant also offers an excellent wine list that has received a Best of Excellence award from the Wine Spectator.
Jory // 2525 Allison Lane, Newberg, OR // website
Before you head back to Portland, if you are a race-car buff, it is worth visiting the World of Speed museum located in Wilsonville. The museum includes an enormous collection of beautifully restored former racing cars, motorcycles and boats.
World of Speed // 27490 SW 95th Avenue, Wilsonville, OR // website
One of our favorite restaurants in Portland is Holdfast, a tiny 16-seat supper club offering a nine-course chef’s menu (with beverage pairing) in a single seating on Friday, Saturday and Sunday nights. The restaurant is located in southeast Portland in the Fausse Piste Winery and has a completely open kitchen so you get a bird's-eye view of all the culinary action. Chefs Will Preisch and Joel Stocks prepare and serve the entire dinner with the assistance of Jeff Vejr, who is responsible for pairing the wines with their creative cuisine. The cuisine reflects the chefs’ affinity for seafood and ocean foraging. Some standouts from a recent dinner included uni with dashi and foraged sea vegetables; halibut with chorizo, tomato and beans and, for dessert, a delicious composed plate consisting of nectarines with cajeta (a Mexican confection similar to dulce de leche), tonka bean purée and brown butter sauce.
Holdfast // 537 SE Ash Street // website