Explore the Scenic Tranquility of Highway 101 on Your Oregon Coast Road Trip

With small towns, craft breweries, and quiet beaches, the Oregon Coast is tailor-made for road-tripping.

The Nestucca River was quiet except for a great blue heron that unfurled its massive wings and flapped away disgruntled every time our kayaks approached. On one side of me was Mike, my best friend and travel companion on my trip down the Oregon Coast. On the other side was Ryan Fox, our eminently personable guide, who, bearded and rugged, looked as you would expect an adventurer to look—except for his toenails, which were painted orange. “My wife did it once, like, three years ago as a joke,” he said. “But I liked how it looked. I guess it stuck.”

As we paddled along in the cool air—despite being early August, it was a pleasant 65 degrees—we watched Fox chase down a renegade beer bottle someone had thrown in the water. We listened as he told us about Bayocean, an early-20th-century “Atlantic City of the West” that fell into the sea after developers failed to account for the erosive effect their work would have on the land.

The breeze picked up; paddling got harder. Fox pointed to a van parked by a modest waterfront house. “That belongs to one of the foremost Bigfoot experts,” he said, before qualifying, “in Oregon.”

Just as the headwind was starting to wear out my arms, the river bent under a bridge, and we came out into a patch of windless, glassy water. Wordlessly, all of us stopped paddling, put our feet up, and drifted back toward the dock where we’d rented the kayaks. The birds broke the quiet with happy calls, and for a few minutes, I forgot that there was anything wrong in the world. When we reached the dock, an annoyed teenager pulled our boats in and informed us that they had already closed for the day. His tone suggested: “I have been standing here for fifteen minutes waiting for you—and then you just stop paddling.”

Oregon’s 362 miles of publicly accessible coastline offer one of the most scenic drives in America. Weaving through one-light beach towns and mountainous conifer forests, past sky-high dunes and rugged sea cliffs, this stretch of U.S. Highway 101 is the state’s less crowded answer to California’s famous Pacific Coast Highway. Oregon is also more affordable than its southern neighbor, which has given rise to a vibe that’s at once inviting and refreshingly offbeat.

Our first stop on the weeklong trip was the northernmost city on the coast, Astoria. Founded as a fur-trading outpost in 1811 by John Jacob Astor—then the richest man in the country—Astoria is the oldest American settlement west of the Rockies. Nicknamed Little San Francisco for its steep hills, fog, and Victorian houses, this port of just 10,000 people has the feel of a much bigger city.

Sitting at the edge of a dock jutting 600 feet into the Columbia River, the Cannery Pier Hotel & Spa was once the site of a fish-packing plant, like many buildings on the waterfront. Astoria was a hub for fishing and canning until the 1970s, and the pier was home to the Union Fishermen’s Co-Operative Packing Co., which was organized by a group of the city’s fishermen, most of them foreign-born, in 1897. From the guest rooms, you can see what those men a century earlier would have seen: boats humming along the busy Columbia, morning mist floating above the water, and the evergreen coast of Washington in the distance. You can also see one big thing they wouldn’t have: the behemoth Astoria-Megler Bridge, completed in 1966, which seems as if it’s crossing right overhead.

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For dinner, we took a short walk to Bridgewater Bistro, a former cannery reimagined as an airy loft with wooden beams and big windows facing the river. I have long held that at restaurants with water views, you can predict the quality of the meal based on how well the staff manages the blinds. Neglect can leave a blinding glare; draw them too readily, and the view might as well be of a parking lot. At Bridgewater, the hostess managed the blinds like a post-op IV drip, carefully calibrating our view of a ship several stories tall making its way down the river as the sunset turned the water orange.

Sure enough, the food was equally thoughtful, with original takes on local favorites, like zesty avocado toast piled with freshly caught Dungeness crab, spritzed with lemon, and served on house-baked French bread. I gloated that my hypothesis had held up, but Mike was not impressed. He suggested that there were more obvious indicators that our meal would be good—like the menu.

In the morning, we borrowed a pair of the hotel’s bikes and rolled down the boardwalk, which runs alongside the trolley tracks into the city center. Like San Francisco’s cable car, the Astoria trolley is today used more for touristing than for transportation. Another similarity to San Francisco: a devastating fire in 1922 forced Astorians to rebuild the city. As we explored, we noticed that much of modern Astoria’s architecture can be traced to that period, with former banks, department stores, and hotels from the 20s and 30s filling up with microbreweries, restaurants, and cafés to feed the burgeoning tourism industry.

Oregon is arguably the craft-beer capital of the United States: the fertile Willamette Valley grows a sixth of the nation’s hops, and the state is home to more than 300 breweries.

The tallest among them is the eight-story, Gothic Revival Astor Building, built in 1924; following a 2015 renovation, it’s now home to apartments and shops, including the Naked Lemon bakery. When we pulled up, owner Aleesha Serrita Nedd welcomed us with lemon-curd vanilla cupcakes, decadently loaded with buttercream and packing an explosive, citrusy punch. “I have to warn people they’re not like grocery-store cupcakes,” Nedd explained with a smile.

We tried (but failed) to pace ourselves as Nedd, a native Astorian, told us about starting the bakery as a pop-up in 2016. Demand grew so quickly that she quit her day job and moved into a storefront, where she serves classics alongside a rotation of originals that play on the Oregonian culinary tradition of weird new combinations. The “gas station French macaron” is perhaps the only gourmet pastry around made from Flamin’ Hot Cheetos and cheddar powder filling.

Like New Yorkers with pizza and Texans with barbecue, Oregonians can be snobs when it comes to beer. That’s because Oregon is arguably the craft-beer capital of the United States: the fertile Willamette Valley grows a sixth of the nation’s hops, and the state is home to more than 300 breweries.

One could build a trip entirely around the superb breweries that populate the coast, but the crown jewel of the regional beer scene, the one that attracts visitors from around the globe, is De Garde Brewing, which, despite its size—the whole operation is only seven people—is frequently ranked among the best in the world.

To visit, we took a windy stretch of Highway 101 an hour and a half south from Astoria. Just after Cannon Beach—which, as the closest seaside town to Portland, is usually the most packed—the day-tripper crowd thinned out, the traffic evaporated, and staggering views of the water popped up at nearly every turn in the cliff-top road. We cut inland to the dairy-farming town of Tillamook, where De Garde’s tasting room is housed in a former Napa Auto Parts store. It seemed like a pedestrian site for a pilgrimage—until we sampled the Broken Truck wild ale, which was unlike any beer I’ve had. Super dry but noticeably hoppy, it tasted like a crisp ale crossed with a white wine.

Head brewer and owner Trevor Rogers explained that he and his wife and co-owner, Linsey Rogers, had backgrounds in wine and decided to bring their knowledge of viticulture to beer. They chose Tillamook because of its climate, which is especially well-suited to spontaneous fermentation, as well as its proximity to the hops and high-end Pinot grapes of the Willamette Valley.

De Garde’s beer is made in wine barrels using native yeast, a painstakingly slow process that takes one to five years to produce a tiny batch. To taste it, you have to come to Tillamook. The result is, as Rogers puts it, “a pretty unique representation of place.”

“This,” Mike said as he wrapped some gauze around his bleeding hand, “is a great hotel.” Shortly after we’d checked in to Headlands Coastal Lodge & Spa, in the fishing town of Pacific City, Mike had cut himself on his razor while rifling around in his suitcase. We called the front desk for some bandages, and the attendant was at our door seemingly a minute later. She was kind and attentive, and appeared deeply concerned about Mike’s hand (far more than I was, having had 20 years of experience watching him injure himself and quickly recover). Her care was indicative of the attention to detail we’d enjoy during our stay.

Our trip led us past too many stunning overlooks and blissfully open state parks to count.

Headlands, a 33-room resort that opened in 2018, sits right on Cape Kiwanda, a state natural area featuring a 240-foot-high sand dune, lots of tide pools, and a public but relatively quiet beach, which after nightfall lights up with campfires. We admired how so many hotel details—locally sourced Douglas fir wood in the lobby, shower curtains that pull back to reveal ocean views, in-room wall racks for bikes and surfboards—served to highlight the landscape.

We took an invigorating ride down the beach on fat-tire bikes we borrowed from the hotel, then met up with the aforementioned Ryan Fox, who leads adventures for Headlands guests. After kayaking, we hiked up the Great Dune at Cape Kiwanda. (“At least that’s what people call it,” Fox said. “It doesn’t really have a name.”) The sandy crests had the wind-smoothed texture of, as Mike put it, the planet Tatooine, “where the Jawas sell the droids to Luke Skywalker.” (You never know when a working knowledge of the topography of Star Wars planets will come in handy.)

From the peak, we took in a dizzying panorama of cliffs, ocean, and forest. Teenagers hurtled down the dune while their friends took pictures. A flock of pelicans—”the hound dogs of the sea,” Fox called them—sat on the water, mirroring a pack of surfers waiting 20 yards away.

After sleeping to the sound of the lapping sea, Mike and I headed out for an early hike at Cape Lookout. A morning drizzle pitter-pattered against the Douglas fir and Sitka spruce overhead, but the canopy was so thick that we barely felt the water. We were told that the loop was sometimes crowded with tourists, but the only sound that morning was our own footsteps, and the lightly falling rain.

Our trip was filled with small towns like Depoe Bay, a whale-watching destination where we spent a night nestled between the woods and a Big Sur–like cove. But the tiniest was the village of Yachats (ya-hots), a quaint mile-long strip bisected by Highway 101. We spent an afternoon perusing the shops and lunched at Yachats Brewing, where we ate chicken-salad sandwiches and drank Thor’s Well IPA, the Yachats take on the unofficial state beverage.

It made sense to follow the beer up with a stop at the actual Thor’s Well, a nearby rock formation where waves spout out like a geyser. We visited around high tide, when the water puts on quite a show, yet had no trouble finding a good vantage point—in part because this corner of Oregon has no shortage of natural attractions. Our trip led us past too many stunning overlooks and blissfully open state parks to count, including the Devil’s Punchbowl, Devil’s Churn, and Devil’s Elbow, which suggest that Satan is a surprisingly big part of coastal geography.

As we approached our final stop, the landscape changed again. Miles and miles of sandy ridges lined the horizon; roadside signs offered ATV rentals to explore the Oregon Dunes National Recreation Area.

The economy of Coos Bay, the most populous city on the coast, has long revolved around logging, but visitors are now arriving in increasing numbers for four-wheeling, hiking, and clamming, and to escape to new accommodations such as Bay Point Landing, a modern camping resort with Airstream suites, RV spaces, and tiny-house lodgings. Our cabin was designed in a chic Scandinavian style, with a private firepit from which to watch the sun set over the bay.

Fifteen minutes south of Bay Point lie three of oceanside state parks, crowned by the storybook Shore Acres. Lumber tycoon Louis J. Simpson built Shore Acres in the early 20th century as a private estate, and its botanical gardens are full of flowers and trees that he collected on his travels around the world. As we walked the well-manicured paths, the tranquil Japanese pond was a calming contrast to the untamed forest and cliffs that flanked the grounds.

That night, back at the cabin, we built a fire, popped open a bottle of De Garde, and toasted our luck at getting the chance to spend so much time together. We sat watching the fire crackle in the pit, the water flowing down the bay, and the seagulls gliding in the wind, all by ourselves.

The Best of Coastal Oregon

Where to Stay

Bay Point Landing: A fun, modern camping resort in Coos Bay. Doubles from $224.

Cannery Pier Hotel & Spa: Set on a dock, this Astoria hotel has stunning views of the Columbia River. Doubles from $299.

Headlands Coastal Lodge & Spa: This 33-room Pacific City resort is one of Oregon’s standouts. Doubles from $500.

Whale Cove Inn: At this boutique property in Depoe Bay, each of the seven rooms has a balcony Jacuzzi overlooking the cove. Doubles from $520.

Where to Eat

Bridgewater Bistro: An airy riverfront restaurant in Astoria that hits the sweet spot between elegant and casual. Entrées $17–$31.

Epilogue Kitchen: En route back to Portland, take the scenic Umpqua Byway to this innovative Appalachian inspired spot in Salem. Entrées $10–$20.

Monkey Business: An unassuming food shack near Coos Bay beloved for its clam chowder. Entrées $7–$18.

Naked Lemon: This tiny downtown bakery is an Astoria favorite for treats such as scones, cupcakes, and macarons.

Restaurant Beck: Whale Cove Inn’s acclaimed fine dining venue offers breathtaking views of waves crashing on the rocks. Entrées $28–$32.

Wayfarer: Try the hot crab sandwich, made with locally caught Dungeness, at this woodsy bungalow in Cannon Beach. Entrées $29–$42.

What to See

Visit one (or two!) coastal brewpubs, such as Astoria’s Fort George; De Garde in Tillamook; Pelican Brewing; or Yachats Brewing.

Then stroll through some of Oregon’s most scenic landscapes. From the beaches at Ecola to the gardens at Shore Acres, the parks along U.S. 101 have something for everyone.

A version of this story first appeared in the June 2021 issue of iBestTravel under the headline Between the Pines and the Pacific.