Stop 1: Portland, Oregon

Portland makes a natural starting point for a Pacific Northwest road trip. Known for its independent spirit, the city blends an acclaimed food scene with lush green spaces and easy access to the outdoors. Travelers can spend the morning wandering through Washington Park’s International Rose Test Garden, sampling coffee from one of the city’s celebrated roasters, or exploring Portland’s vibrant food-cart pods (Hawthorne Asylum Food Cart Pod, Cartopia) before heading out to nearby natural attractions like the Columbia River Gorge or Mount Hood.

Two standout properties offer distinct ways to experience the city, making a strong case for a little hotel-hopping. A lively gathering spot since 1909, the historic Hotel Lucia is beloved for its art-forward interiors and photography collection featuring works from Pulitzer Prize–winning photographer David Hume Kennerly. Plus, it boasts a central location near highlights such as Powell’s City of Books and the buzzy Pearl District, putting guests at the heart of Portland’s creative scene.

Just a few blocks away, Sentinel offers an equally enchanting experience. Spread across two stately early-20th-century buildings, the hotel blends classic architecture with contemporary design and spacious guest rooms. Guests shouldn’t miss the on-site wine lounge or the impressive art collection. While the hotel’s central location puts you within easy reach of Portland’s theater district, you can also borrow one of the hotel’s bikes and cruise along the nearby Willamette River waterfront.

Stop 2: Bend, Oregon

From Portland, head southeast toward Bend, a high-desert destination framed by the snow-capped peaks of the Cascade Mountains. The city has become a magnet for outdoor enthusiasts thanks to its access to year-round recreation—from hiking and mountain biking in the summer to skiing and snowboarding at nearby Mt. Bachelor in winter. The surrounding landscape is just as captivating, defined by ancient lava flows and dramatic volcanic formations, while the nearby Cascade Lakes Scenic Byway leads travelers past alpine lakes, dense pine forests, and sweeping mountain views. That said, carve out some time to wander through Bend's lively downtown, which is teeming with locally owned shops and restaurants.

Riverhouse Lodge sits along a peaceful stretch of the Deschutes River and provides a relaxing base for exploring Bend. Accommodations range from spacious lodge rooms and family-friendly bunk rooms to river-view rooms with fireplaces or private fire pits—perfect for unwinding after a day on the trails. Many rooms feature patios or balconies overlooking the water, where guests can watch kayakers and paddleboarders drift by. After a day of hiking, biking, or brewery-hopping in town, relax beside outdoor fire pits or recharge in the property’s barrel saunas and steam room, or with a soak in the pool or hot tub.

Stop 3: Columbia River Gorge (Stevenson, Washington)

Continuing north toward Washington, the route winds through the Columbia River Gorge, one of the Pacific Northwest’s most scenic stretches of highway. Scenic viewpoints appear around nearly every bend in the road, offering sweeping vistas of the river as it cuts through the mountains. Stops like the iconic Multnomah Falls—Oregon’s tallest waterfall—and the historic Vista House at Crown Point provide especially striking vantage points and some of the region’s most photographed landscapes.

Perched above the Columbia River Gorge in the charming town of Stevenson, Skamania Lodge spans 175 acres and blends classic Pacific Northwest lodge charm with luxe amenities, including the tranquil Waterleaf Spa. Its “backyard” doubles as an adventure playground, with golf, ziplining, axe throwing, aerial courses, and e-bike rides through on-site Skamania Adventures. Guests can refuel at one of the lodge’s three restaurants, including the scenic Backyard Grill. Overnight options range from traditional lodge rooms and suites to treetop treehouses, luxury glamping tents, and private forest cabins and villas.

Stop 4: Woodinville Wine Country

Before reaching Seattle, consider a stop in Woodinville, one of Washington’s premier wine destinations. Located just 30 minutes outside the city, the area has become a hub for the state’s celebrated wine industry, with dozens of wineries, tasting rooms, and restaurants clustered in a picturesque valley. The region is particularly known for bold Cabernet Sauvignon and Syrah produced from grapes grown in eastern Washington’s Columbia Valley. Visitors can spend the afternoon hopping between tasting rooms, touring wineries, or enjoying seasonal farm-to-table cuisine.

Nestled among gardens and walking paths, Willows Lodge offers a serene retreat in the heart of Woodinville wine country. The lodge pairs rustic Northwest architecture with warm interiors, along with amenities such as the Spa at Willows Lodge and the acclaimed on-site restaurant, Barking Frog. Guest rooms are especially inviting, with gas fireplaces, deep-soaking tubs, and private patios or balconies overlooking the grounds. Just steps away, the celebrated Herbfarm adds another memorable dining option, while many of Woodinville’s wineries and tasting rooms are a short stroll or bike ride away.

Stop 5: Seattle, Washington

Set between Puget Sound and Lake Washington, Seattle blends maritime history, a strong arts scene, and an excellent food culture. Visitors can watch fishmongers toss fresh catch at Pike Place Market, take in views from the Space Needle, or stroll along the city’s revitalized waterfront. Neighborhoods like Capitol Hill, Ballard, and Fremont offer a glimpse of Seattle’s creative side, with independent bookstores, live music venues, and standout dining. Also, one of the city’s biggest draws is its proximity to the outdoors: Mount Rainier andOlympic National Parks, and the San Juan Islands are all within reach for a memorable day trip.

Back in Seattle proper, Hotel Max offers a boutique stay in the city center that’s anything but cookie-cutter. The 163-room hotel pays homage to Seattle’s creative culture with rotating installations, music-themed rooms, and a striking art collection, including an original Andy Warhol displayed in the lobby. Guests can also borrow one of the hotel’s bikes to explore nearby neighborhoods, coffee shops, and galleries.

Bonus Stop: Tacoma, Washington

Just south of Seattle, Tacoma is emerging as one of the region’s most intriguing cultural destinations. The city’s revitalized Ruston Way Waterfront stretches along Commencement Bay, offering scenic walking and biking paths, waterfront dining, and sweeping views of Puget Sound and Mount Rainier on clear days. Meanwhile, the Museum District showcases an impressive collection of institutions, including the renowned Museum of Glass,Tacoma Art Museum, and the Washington State History Museum, among others. Alternatively, families and wildlife lovers can visit the Point Defiance Zoo & Aquarium, set within the sprawling Point Defiance Park and overlooking the water.

In Tacoma’s downtown Museum District, Hotel Murano nods to the city’s deep connection to glass art. Named after the famed glassmaking island of Murano, Italy, the hotel displays an impressive collection of contemporary glass pieces throughout its lobby and guest floors. A tucked-away spa offers a quiet place to unwind, while the hotel’s restaurants—bite and BAR960—draw both visitors and locals, especially the latter, where craft cocktails are served alongside striking glass works, including pieces by Tacoma-born artist Dale Chihuly.

Explore more destinations in the Northwest and across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.