A short three hour drive from Seattle, Portland is one of our favorite destinations for many reasons. The picturesque riverfront, bustling downtown, charming neighborhoods, tax-free shopping… we could keep going. We wanted to cover two of the things we love most about Portland: the abundance of wine tasting thanks to its proximity to the Willamette Valley, and the vibrant Portland restaurant scene.

In Portland, the city’s collaborative spirit is taking over in new, fresh ways. Portland’s hospitality industry is community driven at its core, allowing more space and opportunities for entrepreneurs to experiment and thrive in and around the city. Long-standing establishments have become collaborative kitchens, inviting colleagues to use their space to make and serve their food on the days their restaurants are closed. These pop-ups focus on menus that meld recipes and ingredients that span different cultures to create a beautiful fusion of flavor. The ingenuity and resourcefulness of the city’s pop-up culture is taking the dining scene to a whole new level, and is redefining Portland as the “City of Pop-Ups.”

Where to Eat + Drink

Chelo

Chef Luna Contreras is arguably one of the most visible faces on the Portland pop-up scene through consistent collaboration with other food industry friends, farmer’s markets selling her own hot sauces, and hosting pop-ups, like Chelo, which pays homage to the memory of her beloved grandmother. Chelo is known for its flavorful and creative Mexican cuisine, with a focus on elevated street food. Plates are designed to be shared, with our favorites being the Gorditas with local mushrooms, leek, kale, oaxaca cheese, and blue corn masa, as well as the Chilaquiles de Pato which feature a juicy duck confit, roasted carrot, kale, pear queso fresco, and mole negro. A visit to Chelo isn’t complete without trying a Tlayuda, which is a crispy, thin-crust Mexican pizza inspired by one of Oaxaca’s most famous street foods. We loved the one with roasted chicken and chorizo, topped with shishito, purple potato, radicchio, queso oaxaca, and black beans. Stay up-to-date on Chelo here.

Bialy Bird

Located in Lil Dame, the same space where Chelo operates in the evenings, Bialy Bird is a trendy breakfast pop-up that specializes in bialys, which are Polish bread rolls topped with various fixings such as onions or cheese. Their menu changes daily, and we love all of the uniquely delicious bialy topping combinations that they have to offer, such as braised lamb and pickles, shaved potatoes and truffle oil, cacio e pepe, okonomiyaki, apricot with honey and feta, and many more. Bialy Bird also offers bagels with fun schmear flavors, like mushroom marsala, ube and coconut cashew, and bacon rum raisin. Wash it all down with a creamy matcha latte and you have yourself the perfect breakfast. Bialy Bird welcomes walk-ins and pre-orders.

Janken

Where do we even begin? Janken is one of the best restaurants we’ve been to, and for good reason. Easily one of Portland’s most exciting restaurant openings, Janken takes you on a culinary journey through Japanese-Korean fusion cuisine curated by Executive Chef Rodrigo Ochoa. A true gem in the Pearl district, Janken focuses on shared plates, handcrafted cocktails, and embracing a traditional-contemporary blend to create a comfortable upscale dining experience. Their beverage program is outstanding, with an impressive sake selection and exquisite cocktails like The Alchemist with gin, yellow chartreuse, shiso syrup, and umami, and Pineapple Express with pineapple infused mezcal, cointreau, cane syrup, and cardamom bitters. We recommend starting the night with a few small plates, with our favorites being the Kanpachi Crudo with compressed watermelon and nuoc cham vinaigrette, the Steak Tartare with braised mushroom, truffle aioli, and milk bread toast, and the Charred Corn with dry miso and cotija cheese. If you’re a sashimi lover, then you definitely have to order the Chef’s Choice Sashimi. All of the fish is incredibly fresh, with a perfectly soft, melt-in-your-mouth buttery texture.

If you’re looking to splurge, the speciality nigiri are phenomenal. Try the Maguro with foie gras and truffle, the Smoked Wagyu with A5 Japanese beef, uni, and caviar, or The Gunkan with toro, uni, and osetra caviar. Whichever one you order, you can’t go wrong! In terms of entrees, there are so many stunners to choose from. The Seared Scallops with black garlic and sorrel are a crowd pleaser, along with the Miso Black Cod, the Maine Lobster, and the A5 Wagyu Hot Stone. For dessert, there are lots of delicious options like the Creme Brulee with grapefruit and shiso, the Asian Pear Tart with yuzu and vanilla icecream, and our personal favorite, the Chocolate Bar Cake. With a lively atmosphere, gorgeous setting, remarkable service, and phenomenal food, Janken is a must-visit for anyone staying in the Portland area. For more information or to make a reservation, visit their website.

Amaterra Wines

Meaning “for the love of the Earth,” Amaterra is a state-of-the-art winery and restaurant located amidst the tree-filled slopes of Portland’s West Hills with unparalleled views of the Willamette Valley. Just minutes from downtown Portland, Amaterra is a destination for both residents and visitors alike, and features a 12-acre vineyard, chef-driven restaurant, and an outdoor event lawn. They produce 10,000 cases of wine annually, predominantly Pinot Noir and Chardonnay. Amaterra is the perfect spot for wine lovers to get a taste of the Willamette Valley without even having to leave the Portland area. The floor-to-ceiling windows in the tasting room and restaurant offer incredible views of the valley, along with a beautiful outdoor deck that is open year-round. We recommend doing a wine tasting alongside a few small plates or a cheese and charcuterie board. Amaterra also offers an impressive dinner menu. More information here.

Expatriate

Located across the street from Lil Dame, Expatriate is a trendy cocktail bar and lounge that also serves delicious late night bites. Coming from lauded Portland chef, Naomi Pomeroy, Expatriate has fantastic craft cocktails along with sake, wine, and beer. The cocktails rotate seasonally, and they have something for everyone, whether you’re more into gin, whiskey, mezcal, or rum. The James Beard Onion & Butter Sandwich is a crowd favorite, along with global delicacies like the Hot & Sour Indian Spiced Fries and the Crab & Corn Noodles. Expatriate is the ideal late night spot to grab a drink and a snack after dinner, and the vibes are unbeatable.

Heavenly Creatures

Heavenly Creatures is a romantic, moody and feminine wine bar that true wine experts swear by. They offer a fantastic array of European wines and have a very knowledgeable staff. We love that Heavenly Creatures has hard-to-find wines like orange wine and chilled reds. The camembert dip with potato chips is a crowd favorite, as are the yellowtail toast and the pork croquettes. Heavenly Creatures is an intimate space that is perfect for a date night or a catch-up with friends. Please note they only take walk-ins.

Where to Stay

We recommend the Dossier Hotel, which offers travelers a remarkable immersion into Portland’s culture and unique way of living. Part of the renowned Provenance Hotels collection, Dossier embodies the city’s cultural ethos, in harmony with its natural surroundings. Each of Dossier’s art-filled rooms and suites features locally inspired amenities designed to bring the spirit of Portland into the hotel. Dossier is very centrally located in downtown Portland, making it easy to explore the city. They have an on-site bar and restaurant that has a fantastic happy hour. Another perk is that they are dog friendly! For more information or to book a stay, visit their website.

More Things to Do in Portland

• Shop: betsy & iya, Roots & Crowns Apothecary
• Visit: Portland Art Museum, Portland Japanese Garden, The Grotto
• Cruise: Portland Spirit (river sightseeing cruise)