This Is Oregon's Ultimate Early Summer Road Trip

This Is Oregon's Ultimate Early Summer Road Trip

The first time I took a road trip through Oregon was well before I could choose the route, or even to steer the vehicle. I was ten. My mother loaded me into the family's '77 Honda Civic and we drove U.S. Highway 101 all the way to the Canadian Border. What I remember about the Beaver State was mostly about penny candy and tent camping.

Forty years later, half of them in an Oregon I now call home, I've criss-crossed the state a hundred times, and while the coast remains a magical place, it's at the end of a road trip I'd send travelers on. The state is enormous, its bounty of lesser-explored places vast enough to spend a lifetime working one's way from one corner to the next. While most visitors stick to the north-south spine of highway on the west side of the Coast Range, a loop is the pro route, beginning and ending in Portland.

Portland: Sauna Culture And A Late Chef's Legacy

Day one: Portland. The state's largest city is dusting off its bruised post-pandemic reputation of late, with an ever-evolving food, hospitality and sauna scene. Check into Jupiter NEXT, the 67-room boutique hotel in the Central Eastside that grew out of the original Jupiter Hotel, a converted 1960s motor lodge; its lobby bar, Hey Love, and fifth-floor rooftop lounge look out over the Burnside Bridge. Have dinner at L'Echelle, the Oregonian's 2025 restaurant of the year, a French bistro on SE Division that chef Mika Paredes and restaurateur Luke Dirks opened in 2024 as the late Naomi Pomeroy's final project. Paredes remains executive chef as of 2026, still steering the kitchen toward the lighter, ingredient-forward French bistro cooking Pomeroy and Dirks first envisioned.

The next morning, start with a hike in Forest Park, the 5,200-acre urban forest, the largest of its kind in the country, laced with more than 80 miles of trail including the 30-mile Wildwood, before wandering the shelves of Powell's Books, especially if it's rainy out. After lunch at the beloved Burmese Rangoon Bistro if it's a weekend or the buzzy Asian-fusion brunch spot Churn if it isn't. Then book an afternoon sauna session at Knot Springs, the wellness club on the fifth floor of a Burnside building with hot and cold soaking pools, a eucalyptus steam room and a cedar sauna overlooking the Willamette. For dinner, head to Urdaneta, the Basque-inspired pintxos bar on NE Alberta from chef Javier Canteras, who grew up splitting time between Madrid and the Basque Country and serves ham, tortilla and Basque cider straight off a bustling front bar. If you've still got some energy, check the alt weeklies' calendars for some good live music, or go straight to the venue pages: Revolution Hall, Aladdin Theater and Mississippi Studios are three of the best.

On the way out of town, there's always good coffee in the lobby at Jupiter NEXT and for that matter most hotels in Portland, but for an even better glimpse at the city's java cred, head to Extracto's roastery and coffeehouse on NE Killingsworth. You'll only have slid the lid off of the City of Roses' greatness. And you'll be back.

The Columbia River Gorge, Underrated And Uncrowded

Day three: White Salmon. While first-time tourists flock to the coast (with good reason) head east instead, for a hike at Catherine Creek barely on the Washington Side of the mighty Columbia River Gorge, an area scoured down to bedrock by the Missoula floods some 13,000 to 15,000 years ago and now home to more than 90 wildflower species that bloom from late winter into early summer. Afterwards, check into the Society Hotel in Bingen for a sauna and a soak, and a stay if they have space: the 20 cabins on the property, each with its own porch and hammock, ring a central bathhouse with a saltwater soaking pool, hot tub, sauna and cold plunge, and are often fully booked. If that's the case, hit Pixán Taqueria & Cantina in White Salmon for dinner, a Yucatecan-inspired spot known for its tacos and pumpkin-seed salsa, and then head back across the Hood River Bridge, the 1924 vertical-lift span across the Columbia, to Thistledown on Oak, a boutique hotel tucked into the top floors of Hood River's Historic First National Bank building, all antiques and Edwardian-era detail.

If you stayed on the Washington Side, or don't mind popping back across the river for the Gorge's best bakery, start the next morning at White Salmon Bakery, the wood-fired bread and pastry spot on NE Estes Avenue known for its sausage biscuits and Mount Hood-view patio, before another of the area's many good hikes or a whitewater trip on the Lower White Salmon River. Several local companies guide rafters all summer. After one more night in the gorge and maybe another stop at the bakery, it's time to head south, to a land of prehistoric fossils and painted earth.

The Painted Hills And Bend's High Desert Playground

Day five: The Painted Hills to Bend. At early morning or at sunset, the wheat fields along Highway 97 on the road from The Dalles to Shaniko bask a beautiful drive in gold, an idyllic backdrop for a color palate found nowhere else in the West: The Painted Hills. The Painted Hills unit is one of three that make up the John Day Fossil Beds National Monument, along with Sheep Rock and Clarno, and they're all special for different reasons. But if you only get to one, this is the one. Take the day to explore, before heading back west again, to Central Oregon's adventure playground: Bend.

Once a cowboy haunt, thrill seekers from all over have descended on Deschutes County to ski, hike, mountain bike and paddleboard. Which sport you choose depends on the season, but first check into Brasada Ranch, which is a bit outside of Bend proper but worth the drive into town. The 1,800-acre high-desert resort, 900 acres of which are permanently protected open space, has its own equestrian center, an 18-hole golf course and a spa alongside its cabins and suites.

On the other side of Bend, about the same distance away, is Suttle Lake Lodge, which sits on 15.5 acres in the Deschutes National Forest about 13 miles west of Sisters, redesigned several years back by The Mighty Union, the Portland group behind the Ace Hotel, into lodge rooms, rustic camp cabins and lakeside cabins gathered around a fireside Skip Bar and the lakefront Boathouse Restaurant. It's the perfect vantage point for exploring the Metolius River, one of the country's largest spring-fed rivers, which emerges fully formed from springs at the base of Black Butte and runs cold, clear and swift past Camp Sherman toward Lake Billy Chinook, its upper 12 miles restricted to fly-fishing and catch-and-release only.

For dinner, grab some food at Brasada or head into Bend for Bar RBC, the new tapas-inspired project from John Gorham, the chef who helped create Portland's legendary food scene with Toro Bravo before relocating to Central Oregon in 2021: it's a Spanish-driven small plates bar, all sherry, vermut and cocktails, with a few Toro Bravo-era dishes like potatoes bravas folded into the menu alongside Rancher Butcher Chef staples like the 64-ounce txuleton porterhouse. The Bar sits in the former Dogwood Cocktail Cabin space on Minnesota Avenue. For after-dinner drinks, there's a brewery on every corner but the McMenamin's Old St. Francis School is worth a look. One of a handful of Pacific Northwest schools McMenamins has flipped from crumbling classroom into vibey northwest bar, restaurant and/or hotel, this location is a converted 1936 Catholic school. And it's one of the coolest, complete with a salt-water soaking pool tiled with hand-painted scenes of St. Francis.

The next day, grab coffee at Thump, the Bend-founded roastery with locations downtown and at its NW York Drive headquarters, before choosing a hike, from a hundred good options. If it's toasty out, the rough road to Todd Lake leads to a 1.7-mile loop with plenty of good spots to pull up a camping chair and swim awhile. Head back into town for lunch at the Hook & Plow before spending the afternoon in vintage Bend fashion: renting some kind of watercraft from Tumalo Creek Kayak & Canoe and floating the lazy Deschutes River, which cuts right through town. It's a lively scene during the day, at night a way to catch a free concert, if there's a show playing at Hayden Homes Amphitheater that you want to listen to but not so badly that you ponied up for tickets. Dozens of kayaks, rafts and paddleboards will be found on the water, which is not much farther from the stage than the lawn inside the venue.

For dinner, a few good options. There's El Sancho on NE Dekalb Avenue, the taco shop that got its start as one of Bend's original food carts in 2010, or a nice selection of food truck options from Podski, the cluster of roughly ten carts across from the Box Factory that includes everything from Polish pierogi to vegan comfort food.

Bend To Ashland: Two Ways South

Day seven: Bend-Ashland. If you've timed this vacation right, the last morning in Bend will line up with its farmer's market, held on Wednesdays from 11 a.m. to 3 p.m. in Brooks Alley just off Drake Park and an ideal place to grab breakfast, fresh fruit and other provisions for the drive to Ashland, Oregon's southernmost town. There are two ways to do it: the longest route snakes through the lava fields of McKenzie Pass, which is open only from late June through early November, weather permitting (the road typically opens the third Monday in June). The road drops down to a beautiful cold, clear river and to the 80-mile long McKenzie River Trail. Here lies the overwhelmingly Instagrammed (and resultingly often quite crowded) trip to the "Blue Pool," aka Tamolitch Falls. But other sections of the trail are less popular and just as pretty. Carve one out, before continuing along the river towards Eugene. Stop for lunch at Morning Glory Cafe and then to the Sweet Life Patisserie for some of the state's best cinnamon rolls.

The alternate route: head south from Bend to Crater Lake, the state's only National Park and therefore a must for travelers who trust William Gladstone Steel's judgment; the Portland journalist campaigned for 17 years to see it designated, and it finally happened in 1902. The deepest lake in the country at nearly 1,950 feet, it fills the collapsed caldera of Mount Mazama, which erupted roughly 7,700 years ago, and the 33-mile Rim Drive circles the water with overlooks the entire way, including views of Wizard Island, the volcanic cinder cone that rises from the lake's western side. Catch a Shakespeare play. Go to Mäs for dinner, or Nous, the Alsatian restaurant on Main Street co-owned by Molly Shaughnessy, who moved home to Ashland after a few years in Germany and settled on the German-French hybrid cuisine with two friends; it was a hard sell at first ("People were like, 'What's Alsatian?'" she says), but it found its footing fast. For wine, Rob Folin, who makes his own Ryan Rose label while serving as head winemaker at Belle Fiore Winery right in Ashland, is a good introduction to the region's tempranillo, syrah and malbec, grown in a climate whose hot days and cold nights toughen up the grapes the same way Napa's do.

The Wild South Coast

Day nine: The northern coast's beaches are well-known, but the stars of the Oregon Coast lie closer to California. So after checking into Tu Tu' Tun Lodge, the riverfront retreat seven miles up the Rogue from Gold Beach, find a good place to watch the sunset in nearby Samuel H. Boardman State Scenic Corridor, one of the coast's most scenic stretches just up Highway 101, before dinner at the Crazy Norwegian's Fish & Chips, the Port Orford institution known for its fish and chips and marionberry pie. The next day, a couple of good hiking options: one is Blacklock Point, at the end of a trail that feels like a secret, reached from a trailhead off Airport Road in Sixes and ending at a black-sand beach with sea caves. Then for sunset, head back to the Port Orford Heads, the former U.S. Coast Guard lifeboat station that operated from 1934 to 1970 and now houses a small maritime museum, before dinner back at the lodge, where riverside dining, a wood-burning sauna and world-class fly fishing right on the Rogue keep most guests from wanting to leave at all.

The Central Coast's Quiet Riches

Day 11: The central coast is the most underrated stretch, and most travelers tend to blast right by it on their way north. But it's a good idea to spend a couple of days exploring the riches between Florence and Newport. On the way up, duck inland for a short but rewarding hike at Sweet Creek Falls, where four tiered plunges cascade a total of 70 feet along a trail with wooden catwalks bolted to the canyon walls.

Then head to Overleaf Lodge and Spa, where mornings start with a scratch-made breakfast spread that changes daily, plated to order once you let the team know what you're craving. A scaled-back version of the same easy hospitality carries through the Wine Cove in the lobby. If they're booked, try Heceta Head Lighthouse Bed & Breakfast, where an epic seven-course breakfast awaits guests each morning, a friendly ghost may play havoc with your electronics and a magical walk to the base of the lighthouse should close out the night. But first, grab dinner in nearby Yachats at Ona, where chef and owner Michelle Korgan serves a globally inspired, locally sourced menu overlooking the Yachats River. The next day, head to Cape Perpetua, the highest viewpoint accessible by car on the Oregon Coast at 800 feet, with views extending nearly 40 miles out to sea on a clear day. There's an easy and beautiful loop trail at the Discovery Loop, a 1.4-mile forest walk lined with interpretive signs and benches, then a drive to the highest point vehicles can reach on the coast for a bit of while watching. For sunset, it's a quick drive back down to the ocean again, to the Devil's Churn, a roughly 100-foot crevice in the basalt that funnels incoming waves into dramatic bursts of spray.

The North Coast, Without The Crowds

Day 13: Finally it's time to head north, but not the obvious tourist traps that land on most Oregon Coast best of lists. First stop is Lincoln City and the Salishan Hotel, reimagined over the past five years by SCP Hotels, the "Soul Community Planet" collection led by founder Ken Cruse, after the property changed hands more than once in the 2010s and underwent a multimillion-dollar renovation. The hotel is now branded Salishan Coastal Lodge by SCP and leans hard into wellness, with an herb garden supplying its cocktail program and eco-minded touches like lithium-battery golf carts. Over a two-night stay, there's plenty to do on property: golf on the 18-hole Salishan Golf Links, restored in 2004 by Oregon golf legend Peter Jacobsen with ocean-view holes carved through old-growth timber, have seafood at The Attic, the resort's farm-to-fork dining room. Catch the lodge's new beach shuttle, which now runs daily to a private stretch of coastline, to a beach that feels private, even though all Oregon beaches have been public since 1967, when Governor Tom McCall signed the Oregon Beach Bill. Ask nicely (and pay for it) and the hotel will set up its Vintage Land Rover beach picnic, a curated spread driven out to a secluded spot with sweeping coastal views. The only requirement is that you book a massage or facial at the Salishan Spa, where therapists punch high above their weight for a market as small as the central coast.

Day 15: Beeline for Pacific City, where the Headlands Coastal Lodge & Spa awaits. The hotel sits inside Cape Kiwanda State Natural Area with oceanfront balconies, a spa and Meridian Restaurant & Bar. The spa's newest treatment is the Marine Moisture Drench, a full-body kelp wrap that hydrates and replenishes with ocean-derived minerals, and the property's Adventure Coaches can arrange cold water surfing, kayaking on the Nestucca River, dory boat fishing, clamming in the bay and guided hikes up the Great Dune. For mountain bikers, a brand new trail system opened near Pacific City in August 2026, built by the Tillamook Off-Road Trail Alliance and adding nearly seven miles of rideable singletrack, with plans for roughly 28 miles more between Pine Grove and Fritsche Cabin in the next couple of years. But there are also a plethora of stellar hikes: the Pacific City Pathways Loop, a 1.2-mile ramble through Douglas fir plantation and old-growth forest that starts a short walk from the lodge, and the guided routes at Two Rivers Trail and Sitka Sedge Natural Area. For dinner, stay in: Meridian serves Northwest cuisine sourced from local farms and the property's own Mary's Herb Garden, with dining-room views of Haystack Rock. The next day, head to Manzanita, the crunchier cousin to upscale Cannon Beach, for a stroll around the impossibly cute town: browse the local art at Hoffman Center for the Arts, walk the seven miles of beach beneath Neahkahnie Mountain, the peak whose views are said to have convinced Governor Oswald West that Oregon's beaches should stay public forever, and pop into the farmers market if it's summer. Grab lunch at the Manzanita Grocery and Deli before heading up the coast to Cannon Beach for dinner at Screw and Brew, the beloved combo hardware store and pub known for its halibut burger and oyster shooters. After dinner, sweat it out at Loma Sauna House, which just opened in July 2026 and is already the best sauna and cold plunge setup on the coast; it's the vision of acupuncturist Sandy Riedman, built around a Finnish-inspired hot-cold circuit of cedar sauna, eucalyptus steam and cold plunge.

One Last Stop North: Astoria

Day 17: Astoria. Before turning inland for wine country, push north to the oldest American settlement west of the Rockies and the coast's most cinematic town, the backdrop for enough films over the decades that Astoria has its own devoted movie-tourism circuit. Stay at the Herondale Hotel, a 39-room boutique hotel that opened in July 2026 on a bluff above the Columbia River, on land where Lewis and Clark camped near the end of their expedition west. The design leans on bespoke furnishings and natural materials pulled from the surrounding coastline, and the communal spaces are built around farm-to-table small plates, wine and beer, and outdoor hot-and-cold water therapy. The hotel connects directly to Astoria's Riverwalk, which winds past a nature preserve before opening onto a six-mile waterfront path into the historic downtown. Spend the afternoon wandering the Victorian core, all restaurants, galleries, coffee shops and independent shops, before heading back to the hotel for dinner and a soak. The Herondale is expected to roll out new spa and dining programming over the next year, along with experiential offerings built around Oregon's artisans.

Oregon Wine Country

Day 19: After nearly a week on the coast, it's time to head back inland again and explore Oregon wine country, which is home to some of the state's finest hotels. For a boutique, it doesn't get much better than Inn The Ground, a nine-room farmstay built into a hillside on 500 acres of regenerative farmland outside Carlton, where breakfast comes straight from the property's own gardens. If you're looking for a spot with more on-site amenities — think an 85-room main lodge, a full-service spa and JORY restaurant — the Allison Inn is a LEED Gold-certified resort on 35 hillside acres outside Newberg. For a property with award-winning grapes right on the grounds, it's Grange Estate, the nine-room residence next door to The Four Graces Winery in the Dundee Hills.

For dinner, Hayward is the destination meal of the whole valley: chef Kari Kihara's James Beard-nominated New Northwest cooking, relocated from McMinnville to Carlton in 2025. A few doors down on Main Street, chef Kari Shaughnessy — no relation, an easy mix-up in a town this size — just opened Lucky Duck, a café, home shop and short-term rental inside a restored 1920s bank building, pouring Summon Coffee and stocking Revel Meat Co. charcuterie alongside cookbooks and local wine.

Save the next day for tasting, and pick your version of the valley's range. Evening Land Winery pours biodynamically farmed pinot noir and chardonnay off the historic Seven Springs Estate Vineyard in the Eola-Amity Hills. Stoller Family Estate, the 400-acre Dundee Hills property, is home to both the largest contiguous vineyard in the appellation and the world's first LEED Gold-certified winery. And Sokol Blosser is the valley's organic pioneer: the Blosser family planted its first vines in 1971, opened Oregon's first tasting room in 1978, and still farms its 72-acre estate organically today, now with a second and third generation of the family running it.

Back To Portland

Day 21: After more than two weeks on the road, it's back to the big city. Check into Cascada, the underground thermal spa and hotel that opened in the Alberta Arts District in 2025 with four soaking pools, a sauna and a steam room, for a soak and sauna session in the city's newest hospitality offering; the spa also runs a full menu of massages and facials if you want to make an afternoon of it. Since it opened, Cascada has added more programming around its solar-heated conservatory and movement studios, and the restaurant, Terra Mae, has become a destination in its own right, a Portuguese-Japanese spot from chef Megan Sky serving tuna tartare with ponzu and truffle, linguiça croquettes and duck confit with scallion pancakes. If the sun is still out, check out Pal's on Hayden Island, where the team behind Sisters' Suttle Lodge recreated the magic of their Boathouse restaurant on the Columbia: a dockside fish shack with 50 seats inside and 250 more on the patio, a raw bar and oyster towers, and views of the marina out front. For after-dinner cocktails, head across the river to The Malarkey, the wood-fired Pacific Northwest steakhouse from chef Brian Malarkey, who grew up on an Oregon farm and made his name on "Top Chef" before opening restaurants across the country; his new Pearl District spot leans into playful, immersive rooms, including one styled after Portland-born military aviator Hazel Ying Lee.

The next day, explore Alberta Arts, an always vibrant neighborhood that stretches along NE Alberta Street with galleries, shops and restaurants from James Beard-winning chefs. Get coffee at Proud Mary, the Melbourne-born cafe on Alberta known for its single-origin pour-overs and ricotta hotcakes. Then brunch, at Churn, the Asian-fusion cafe on N Mississippi Avenue known for its kimchi hash, pandan lattes and ube French toast. For dinner, walk a few blocks over to Killingsworth Street for the city's best barbecue, at Podnah's, the Texas-style pit opened in 2006 by Waxahachie native Rodney Muirhead. That leaves just one more stop before this epic Oregon road trip comes to a close: Bauman's on Oak, the cidery in the former Base Camp Brewing space on SE Sandy Boulevard, where Gervais-based Bauman's Cider Co. runs 30 draft lines of its own farm ciders alongside a kitchen from chef Daniel Green, previously of Cafe Olli.

Day 22: Depart. If you've picked a late flight, get to Portland International Airport early, partly to make your dad happy but also because the renewed space has an impressive post-security collection of local representation of the region's food scene. The newest is Straightaway Cocktails' 1,000-square-foot lounge in Concourse C, which opened in June 2026 with a 32-seat bar, an airport-exclusive Bloody Mary and a Roma Spritz made in collaboration with Alaska Airlines, plus Italian bites from a partnership with local bakery Sebastiano's.