The Ideal Weekend Escape to Portland, Oregon

Portland is a city that I find myself returning to time and again. While it may be small, each visit uncovers a fresh perspective or introduces me to another beloved restaurant, café, or bar to reminisce about, along with the ever-present warmth of its locals and the lush, green landscapes filled with ferns. That's why I was thrilled to revisit and spend a few days there with my colleagues at Dinogo this past spring.

The city's size and atmosphere make it incredibly inviting, with neighborhoods that often resemble quaint small towns and outdoor adventures readily accessible both within the city and in the nearby areas. Whether you're seeking a relaxed urban retreat or a blend of city and nature, this Northwest gem has it all. Here's how to enjoy a weekend in Portland, Oregon—drawing from both new spots and beloved favorites we explored.

Accommodations in Portland

Though Portland's neighborhoods, like Northeast Portland's Alberta Arts District and Southeast's Hawthorne, offer fun lodging options, most Airbnbs are located outside the city center. Our top hotel picks are situated in or near the Pearl District, as well as just across the Burnside Bridge in East Portland. Here are some of the finest places to stay in Portland:

Kex

If you're looking to stay in East Portland, Kex Hotel is the ideal choice, offering a blend of private bunk rooms (with shared bathrooms) and en suite king, queen, and double rooms. The 29 accommodations and communal spaces boast a vintage eclectic style—think exposed brick, gallery walls adorned with thrifted art, and cozy leather sofas—that creates a warm, urban atmosphere. To fully enjoy the social scene, be sure to visit the vibrant downstairs bar and restaurant, Pacific Standard, or the seasonal rooftop bar, the Sunset Room, before unwinding in the sauna.

Woodlark

Upon entering Woodlark, located in the heart of downtown, you'll be greeted by a lively lobby bustling with trendy Portlanders and an abundance of houseplants. While the shared spaces buzz with energy, the 150 guest rooms—situated in two interconnected buildings that have been part of downtown Portland since the 1900s—provide a peaceful escape, featuring soothing color palettes, plant-themed wallpaper, and plush velvet armchairs. In contrast, the downstairs bar, Abigail Hall, which was once the Ladies Reception Hall of the old Cornelius Hotel from 1907, radiates vibrant colors. For an exceptional experience, consider booking one of the two-level loft rooms, boasting soaring windows and chic velvet decor.

Ritz-Carlton (opening summer 2023)

• Location: Downtown | Google Maps

The city's upcoming major hotel launch is set to be a transformative addition: The Oregonian-owned Ritz-Carlton, Portland will begin accepting reservations on July 14, 2023, for stays starting in August, aiming to elevate luxury accommodations in the Pacific Northwest. Once open, it will feature 251 rooms and suites located on floors 8 to 18 of a 35-story mixed-use structure. With its height, guests will enjoy breathtaking views of Mount Hood, Mount St. Helens, Mount Rainier, and Mount Jefferson, all complemented by a design that embodies the essence of the Pacific Northwest—think framed images of lush forests and chandeliers inspired by falling rain.

A generous Ritz-Carlton club floor and a gym designed with input from the NBA (thanks to the Trailblazers!) promise to delight fitness enthusiasts. The 19th floor will boast an indoor pool, making it the only hotel in the city to offer this feature. Additionally, the hotel is involved in meaningful urban revitalization initiatives alongside the city and various organizations, including the reimagining of the park at the neighboring O’Bryant Square.

Dining Options

If there's one thing that puts Portland on the global map, it's its outstanding culinary landscape, which has garnered international recognition for years. If you haven't visited yet, be sure to check out some of the city's iconic food highlights—coffee from Stumptown, doughnuts from Voodoo Doughnuts, breakfast at the Saturday Farmers’ Market, and the numerous food carts (with Nob Hill Food Carts being a lovely, centrally situated collection). We also recommend including some exciting newcomers in your food itinerary.

Coffee

This coffee-loving city boasts an abundance of fantastic cafés, with recent newcomers like Nossa Familia and Portland Cà Phê. Both are fourth-wave coffee shops, meaning they source their beans directly from farmers in Brazil and Vietnam, respectively. For a tasty bite, enjoy a cheese-stuffed pão de queijo waffle at Nossa or a bánh mì from Cà Phê.

Brunch

Still feeling hungry? Treat yourself to brunch at the Korean-inspired spot, Toki—be sure to try its steamed bao burger made with a dry-aged beef patty and American cheese—or indulge in freshly made conchas and other delightful Mexican pastries at Matutina.

Dinner

Reserve a table at one of the city's exciting new eateries, like the Southern Mediterranean-inspired Dolly Olive, which features a must-try braised short rib arancini. Enjoy flavorful Malaysian street food at Oma’s Hideaway, upscale Korean-Japanese fusion at Janken, and unforgettable Mexican dishes at Clandestino, known for its weekly pop-up at Lil’ Dame. Also worth mentioning is Tercet, where the nine-course tasting menu changes with the seasons, and Kann, a 2022 Haitian restaurant from Top Chef finalist Gregory Gourdet that highlights Pacific Northwest produce and is a 2023 James Beard Award finalist for “Best New Restaurant.”

For plant-based options, visit Workshop Food & Drink, a Cuban restaurant that impressed us with its savory vegan caviar and beet tartare.

If you're in the mood for something more laid-back, here’s a hot tip: Portland is a renowned pizza city—some even call it the best pizza city in the U.S. Whether you agree or not, it's definitely worth trying a slice from the local scene at Dimo’s Apizza, which opened in East Portland in 2020 and serves a delicious cacio e pepe pie.

Where to drink

With Oregon being home to some of the finest craft breweries in the country and the nearby Willamette Valley, renowned for its cool-climate pinot noirs, it’s no wonder Portland boasts fantastic drinking spots.

A noteworthy addition to the beer scene is Grand Fir Brewing, where brewmaster Whitney Burnside—who became the city’s first female head brewer in 2015—crafts a remarkable East Texas lager. Meanwhile, Gabriel Rucker’s Canard bistro (opened in 2018) continues to set the standard for happy hour.

Whiskey aficionados should reserve a spot at the high-ceilinged, atmospheric Multnomah Whiskey Library, a members-only bar featuring nearly 2,000 spirits from around the globe. Its ambiance rivals some of the top cocktail bars we've visited, and the unique approach—where profits from select cocktails benefit organizations like National Network of Abortion Funds, Planned Parenthood, and Columbia Riverkeeper—makes it a truly Portland experience.

Activities to Enjoy in Portland

Between your meals and drinks, explore the artistic and natural beauty of Portland with these highlights:

Embark on a hike through Forest Park

Oregon boasts stunning natural beauty, and you don’t have to venture far to experience it. Spanning 5,200 acres, Forest Park is one of the largest urban parks in the U.S., nestled within Portland’s boundaries and featuring over 32 miles of hiking and biking trails. As senior deputy editor Jenn Flowers reflects on her visit, "Wandering among the moss-draped Douglas firs, western hemlocks, and big leaf maples, I felt as if I had truly escaped the urban sprawl without actually leaving the city."

Browse for books at Powell’s Books

Portland—and the wider Pacific Northwest—is a haven for avid readers, with one of their beloved sanctuaries being the independent Powell’s, the largest new and used bookstore globally. It’s a must-visit for bibliophiles of all ages and tastes.

Enjoy a leisurely stroll and sip tea at the Portland Japanese Garden

For those who prefer a more serene outdoor experience, visit the Portland Japanese Garden. Established in 1963, it offers a tranquil escape to reconnect with nature and delve into Japanese culture through its remarkable features—centuries-old arches and sculptures gifted from Japan, waterfalls, koi ponds, a zen rock garden, and bonsai trees—as well as the art and cultural events held at its Cultural Village.

Explore the Portland Art Museum

Nestled just steps away from Portland State University, the Portland Art Museum is the largest in Oregon and one of the nation’s oldest art institutions. Established in 1892, it features two historic buildings. Among its renowned works are Claude Monet’s Waterlilies (1914) and Vincent Van Gogh’s Ox-Cart (1884), alongside an impressive collection of Northwest and Native American art. Additionally, it hosts Numberz FM, Portland’s first and only Black-led radio station.

This story was reported with contributions from Jenn Flowers, Katherine LaGrave, and Bailey Berg.