Discover the Tranquil Side of Highway 101 on a Scenic Oregon Coast Road Trip

The Nestucca River was serene, save for a great blue heron that flapped away with annoyance each time our kayaks drew near. On one side sat Mike, my best friend and travel buddy for this Oregon Coast adventure. On the other was Ryan Fox, our charming guide, whose rugged beard matched the adventurous spirit—though his toenails, painted orange, were an unexpected twist. "My wife painted them as a joke three years ago," he chuckled. "I actually liked it, so it stuck around."

As we paddled through the refreshing air—remarkably cool at 65 degrees for early August—we watched Fox dash after a rogue beer bottle that someone had tossed into the river. He regaled us with tales of Bayocean, a once-thriving early-20th-century "Atlantic City of the West" that succumbed to the ocean after developers overlooked the land’s natural erosion.

The breeze picked up, making paddling more challenging. Fox gestured toward a van parked beside a modest waterfront home. "That belongs to one of Oregon's leading Bigfoot experts," he noted, adding, "well, in Oregon, anyway."

Just as the headwind began to exhaust my arms, the river curved under a bridge, revealing a tranquil stretch of glassy water. Silently, we all ceased paddling, propped our feet up, and floated back toward the dock where we had rented our kayaks. The cheerful calls of birds shattered the silence, and for a brief moment, I forgot the troubles of the world. Upon reaching the dock, a frustrated teenager pulled our boats in, informing us they had already closed for the day. His expression clearly conveyed: "I've been waiting for you for fifteen minutes—why did you just stop paddling?"

Oregon boasts 362 miles of publicly accessible coastline, providing one of the most picturesque drives in America. This route along U.S. Highway 101 takes you through quaint beach towns and mountainous conifer forests, past towering dunes and rugged cliffs, serving as a less crowded alternative to California's iconic Pacific Coast Highway. Oregon’s more affordable atmosphere contributes to a welcoming and refreshingly unique vibe.

Our first destination on this weeklong adventure was Astoria, the northernmost coastal city. Established as a fur-trading post by John Jacob Astor in 1811—who was then the wealthiest man in America—Astoria holds the title of the oldest American settlement west of the Rockies. Often called Little San Francisco for its steep hills, fog, and Victorian architecture, this port city, with a population of just 10,000, feels much larger.

Located at the end of a dock extending 600 feet into the Columbia River, the Cannery Pier Hotel & Spa was formerly a fish-packing plant, much like many buildings along the waterfront. Astoria was a bustling center for fishing and canning until the 1970s, and this pier served as the home of the Union Fishermen's Co-Operative Packing Co., established by local fishermen—many of whom were immigrants—in 1897. From the hotel rooms, you can gaze out at the view these fishermen saw a century ago: boats navigating the busy Columbia, morning mist hovering over the water, and the lush coast of Washington in the distance. You can also spot one major feature they wouldn’t have recognized: the massive Astoria-Megler Bridge, completed in 1966, towering above.

For dinner, we strolled over to Bridgewater Bistro, a transformed cannery now featuring a spacious loft with wooden beams and large windows overlooking the river. I've always believed that in restaurants with waterfront views, the quality of the meal can often be gauged by how the staff handles the blinds. Poor management can create a glaring distraction; if they’re drawn too frequently, you might as well be looking at a parking lot. At Bridgewater, the hostess adjusted the blinds with precision, ensuring we had the perfect view of a towering ship gliding down the river as the sunset cast an orange glow on the water.

True to form, the food was equally creative, showcasing unique spins on local classics, such as zesty avocado toast topped with freshly caught Dungeness crab, spritzed with lemon, and served on house-baked French bread. I couldn’t help but feel vindicated in my theory, but Mike wasn’t convinced. He pointed out that there were clearer signs of a great meal—like the menu itself.

In the morning, we borrowed a couple of bikes from the hotel and cruised down the boardwalk, which runs parallel to the trolley tracks leading into the city center. Much like San Francisco’s cable car, the Astoria trolley is now more of a tourist attraction than a mode of transport. Astoria shares another resemblance with San Francisco: a catastrophic fire in 1922 led residents to rebuild the city. As we pedaled around, we noticed that much of Astoria’s modern architecture dates back to that rebuilding era, with former banks, department stores, and hotels from the 1920s and 30s now housing microbreweries, restaurants, and cafés to cater to the growing tourism scene.

The tallest of the bunch is the eight-story Astor Building, a stunning Gothic Revival structure completed in 1924. After a renovation in 2015, it now houses apartments and shops, including the delightful Naked Lemon bakery. Upon our arrival, owner Aleesha Serrita Nedd greeted us with lemon-curd vanilla cupcakes, lavishly topped with buttercream and bursting with citrus flavor. "I have to warn you, they’re not your typical grocery-store cupcakes," Nedd said with a grin.

We tried to pace ourselves, but Nedd, a lifelong Astorian, shared the story of how she launched the bakery as a pop-up in 2016. Demand surged so quickly that she left her day job and opened a storefront, where she offers classic treats alongside innovative creations that explore Oregon’s culinary quirks. The "gas station French macaron," made with Flamin' Hot Cheetos and cheddar powder filling, is likely the only gourmet pastry of its kind.

Much like New Yorkers with their pizza and Texans with barbecue, Oregonians can be quite particular about their beer. This is no surprise, given that Oregon is often hailed as the craft-beer capital of the United States: the fertile Willamette Valley produces a sixth of the nation’s hops, and the state boasts over 300 breweries.

A journey could easily center around the exceptional breweries along the coast, but the standout of the local beer scene, drawing visitors from across the globe, is De Garde Brewing. Despite having a small team of just seven, it's consistently ranked among the finest in the world.

To reach it, we drove a winding section of Highway 101 for an hour and a half south from Astoria. Just past Cannon Beach—the nearest coastal town to Portland and typically bustling with day-trippers—the crowds faded, traffic lessened, and breathtaking ocean views emerged around nearly every bend of the cliffside road. We turned inland to Tillamook, the dairy-farming town that houses De Garde's tasting room in a former Napa Auto Parts store. It might seem an unremarkable location for a pilgrimage—until we tasted the Broken Truck wild ale, which was unlike any beer I'd experienced. It was incredibly dry yet distinctly hoppy, reminiscent of a crisp ale blended with white wine.

Trevor Rogers, the head brewer and co-owner, shared that he and his wife, Linsey Rogers, have backgrounds in wine and aimed to infuse their viticulture expertise into brewing. They chose Tillamook for its favorable climate for spontaneous fermentation and its proximity to both hops and premium Pinot grapes from the Willamette Valley.

De Garde's beer is crafted in wine barrels with native yeast, a labor-intensive process that can take anywhere from one to five years to create a small batch. To experience it, a visit to Tillamook is essential. The outcome is, in Rogers' words, "a distinctly unique expression of the region."

"This," Mike remarked as he wrapped gauze around his bleeding hand, "is an excellent hotel." Shortly after checking into the Headlands Coastal Lodge & Spa in Pacific City, Mike had accidentally cut himself on his razor while rummaging through his suitcase. We called the front desk for bandages, and the attendant arrived at our door seemingly within a minute. She was attentive and kind, appearing genuinely worried about Mike's hand (much more than I was, having spent 20 years witnessing his mishaps and swift recoveries). Her attentiveness was a clear reflection of the exceptional service we would enjoy throughout our stay.

Headlands, a 33-room resort that opened in 2018, is nestled right on Cape Kiwanda, a designated natural area boasting a 240-foot-high sand dune, numerous tide pools, and a public beach that remains relatively tranquil, lighting up with campfires after dark. We appreciated how many details in the hotel—like the locally sourced Douglas fir in the lobby, shower curtains that reveal ocean views when pulled back, and in-room racks for bikes and surfboards—enhanced our connection to the landscape.

We enjoyed an energizing ride along the beach on fat-tire bikes borrowed from the hotel, then reunited with Ryan Fox, who leads excursions for guests at Headlands. After our kayaking adventure, we hiked up the Great Dune at Cape Kiwanda. ("That’s just what people call it," Fox explained. "It doesn’t actually have an official name.") The sandy peaks had a wind-sculpted surface reminiscent of, as Mike described, the planet Tatooine, "where Jawas sell droids to Luke Skywalker." (One never knows when a grasp of Star Wars geography will come in useful.)

At the summit, we were greeted by a breathtaking vista of cliffs, ocean, and forests. Teenagers raced down the dune while their friends snapped photos. A group of pelicans—"the hound dogs of the sea," as Fox referred to them—floated on the water, mirroring a cluster of surfers waiting just 20 yards away.

After drifting off to the soothing sounds of the sea, Mike and I set out for an early morning hike at Cape Lookout. A gentle drizzle pattered against the Douglas firs and Sitka spruces overhead, but the dense canopy shielded us from most of the moisture. We had been warned that the loop could be bustling with tourists, yet that morning, the only sounds we heard were our footsteps and the soft rain.

Our journey took us through charming towns like Depoe Bay, a whale-watching hotspot where we spent a night surrounded by woods and a cove reminiscent of Big Sur. The smallest gem was Yachats (pronounced ya-hots), a delightful mile-long village divided by Highway 101. We spent an afternoon exploring the local shops and enjoyed lunch at Yachats Brewing, feasting on chicken-salad sandwiches and sipping Thor's Well IPA, Yachats's twist on the unofficial state drink.

It was only fitting to continue our beer adventure with a visit to the actual Thor's Well, a nearby rock formation where waves erupt like geysers. We arrived at high tide, when the spectacle is at its best, yet found it easy to secure a great viewing spot—partly because this region of Oregon is teeming with natural wonders. Our journey led us past countless breathtaking overlooks and blissfully open state parks, including the Devil's Punchbowl, Devil's Churn, and Devil's Elbow, which hint that Satan has a surprisingly prominent role in coastal geography.

As we neared our final destination, the landscape shifted once more. Endless stretches of sandy ridges stretched across the horizon, with roadside signs advertising ATV rentals to explore the Oregon Dunes National Recreation Area.

Coos Bay, the largest city on the coast, has historically depended on logging for its economy. However, it is now attracting more visitors for activities like four-wheeling, hiking, and clamming, as well as for modern accommodations such as Bay Point Landing, a contemporary camping resort featuring Airstream suites, RV sites, and tiny-house rentals. Our cabin was styled in a chic Scandinavian design, complete with a private firepit for watching the sunset over the bay.

Just fifteen minutes south of Bay Point, three oceanfront state parks await, with Shore Acres standing out like a scene from a fairy tale. Built in the early 20th century by lumber magnate Louis J. Simpson as a private estate, Shore Acres boasts botanical gardens filled with flowers and trees collected from his global travels. Strolling along the meticulously maintained paths, we found the serene Japanese pond a peaceful contrast to the wild forest and cliffs surrounding the estate.

That evening, back at our cabin, we kindled a fire, uncorked a bottle of De Garde, and celebrated our good fortune in spending quality time together. We relaxed by the crackling firepit, watching the water flow through the bay and seagulls soar gracefully in the breeze, enjoying our solitude.

The Highlights of Coastal Oregon

Accommodations Guide

Bay Point Landing: A vibrant, contemporary camping resort located in Coos Bay. Rates start at $224 per night.

Cannery Pier Hotel & Spa: Nestled on a dock, this Astoria hotel offers breathtaking views of the Columbia River. Rates start at $299 per night.

Headlands Coastal Lodge & Spa: This 33-room resort in Pacific City is among Oregon's finest. Rates begin at $500 per night.

Whale Cove Inn: This charming boutique hotel in Depoe Bay features seven rooms, each with a balcony Jacuzzi offering stunning views of the cove. Rates start at $520 per night.

Dining Recommendations

Bridgewater Bistro: A bright, riverside restaurant in Astoria that perfectly balances sophistication and a laid-back vibe. Entrées range from $17 to $31.

Epilogue Kitchen: On your way back to Portland, detour along the scenic Umpqua Byway to discover this inventive Appalachian-inspired eatery in Salem. Entrées priced between $10 and $20.

Monkey Business: A humble food shack near Coos Bay, famous for its delicious clam chowder. Entrées range from $7 to $18.

Naked Lemon: This quaint bakery in downtown Astoria is a local favorite, known for its delicious scones, cupcakes, and macarons.

Restaurant Beck: Located at Whale Cove Inn, this highly regarded fine dining establishment boasts stunning views of crashing waves. Entrées are priced between $28 and $32.

Wayfarer: Enjoy the hot crab sandwich made with fresh Dungeness crab at this cozy bungalow in Cannon Beach. Entrées range from $29 to $42.

Must-See Attractions

Explore coastal brewpubs like Astoria's Fort George, De Garde in Tillamook, Pelican Brewing, or Yachats Brewing.

Take a leisurely stroll through some of Oregon's most breathtaking landscapes. From Ecola's stunning beaches to the vibrant gardens at Shore Acres, the parks along U.S. 101 offer something for everyone.

This article first appeared in the June 2021 issue of Dinogo, titled Between the Pines and the Pacific.