You could drive straight from Portland to the as-yet-unspoiled Cannon Beach, but you’d be missing out on so much in between.

Astoria

After two hours of driving west from Portland, you might look out at the vast expanse of water on Astoria’s doorstep and think, “There she is, we’ve finally hit that sweet Pacific Ocean,” or “Wow, what a big lake”—but both comments would embarrass you at the town hardware store. You’re at the mouth of the Columbia River, whose bending trail you loosely followed along Highway 30. It has a basin the size of France and a shifting sandbar that makes it one of the most dangerous stretches of waters to navigate in the world—but more on that later. On the mainland, this Victoria-meets-Mount Pleasant downtown (population just south of 10,000) is a fabulously concentrated few blocks of hipster shops and craft libations.

What to Eat and Drink in Astoria

Road trips are hungry work, so get to Buoy Brewing ASAP for a plate of pan-fried oysters with jalapeno jam and goat cheese served alongside a flight of seasonal suds (opt for the India Pale Lager, which satisfies our thirst for hops—Northwest Citra, El Dorado and Idaho 7—but goes down easy). This place is worth a visit based on the location alone: the building was a 90-year-old defunct fish cannery before local arborist and entrepreneur Luke Calvin renovated it into what must be the most well-positioned craft brewery in the U.S. (on a dock, overlooking the water, complete with a window to the lounging sea lions below).

Buoy Beer Company Walking back into town, head to Duane Street and 13th for the locus of edible attractions. The corner opens up to food trucks (like Hot Box BBQ and Mai Ton Thai Food) with picnic tables and an inside/outside-minded Reach Break Brewing. But our favourite stop is just across the street, at Pilot House Distilling. The small distillery’s Bar Pilot vodkas are named after the expert local pilots (often salty senior citizens) who were air-dropped onto visiting ships to steer them into port through the treacherous river mouth, also called the “Graveyard of Ships.” Hi-vis pilot jackets and ring preservers decorate the intimate room, warm and cozy with a long wooden bar, black paint and vintage floral rugs. This is the place to sip chai or jalapeno-lime infused spirits (flights of three are $6), and tastings come with proprietary Bloody Knuckles bloody Mary mix or hand-crafted vinegars like orange ginger and strawberry black pepper. Pilot House Distilling

Where to Shop in Astoria

Astoria feels a lot like Tofino—it’s bursting with young 30-something entrepreneurs who’ve been priced out of the big city. Portland ex-pat Chelsea Johnsen brought her cool vibes and metropolitan tastes to Astoria a few years ago to set up Doe and Arrow, a boutique selling new/vintage clothing, accessories (from small-batch handmade soy candles to southwestern thunderbird-patterned blankets) and records. Speaking of textiles, you won’t believe your eyes when you see the selection of Turkish towels and blankets at nearby store Chariot. This spot also carries the choicest collection of monochromatic handwoven geometric pillows, woven baskets and hand-thrown ombré stoneware. The art deco facade at Astoria Vintage Hardware on the main drag begs a visit—inside awaits an expansive collection of vintage desks, doorknobs, cabinetry hardware and Missouri-crafted bath goods. Chariot Astoria

Your Night Out in Astoria

If you’re staying the night, poke your head into the Voodoo Room. What looks like a rough-around-the-edges biker bar actually hosts some cool up-and-coming live bands on its corner stage. The decor is dusty vintage knickknacks (He-Man dolls, an arcade game doubling as a table), and finding a seat may be an issue.

Cannon Beach

Ah, the main event. The thing about Cannon Beach is that it’s exactly 150-percent more stunning in person than it is in the best Instagram photos. The broken-dinosaur-teeth-like fragments of rock (Haystack the star among them) are the only interruptions in a vast landscape that is otherwise misty blue ocean and wispy grass-framed sand. Simply walking the beach is vacation enough—the ocean physically draws your cares about work emails from you with the same sucking force as a dementor extracting a soul.

Where to Stay in Cannon Beach

First off, you only live once, so you’re staying in a Stephanie Inn beachfront room that’s 28 barefoot steps in soft sand to Cannon’s shores. Between the heavenly Tempurpedic-style foam king-size, the spa Jacuzzi bathroom and ocean surf soundtrack, your stay will be restful AF. Outside your room, there’s complimentary wine and beer gatherings, house-made nightcaps in the library, and a Tesla and driver on hand to take you into/out of town (which comes in handy as there isn’t local transit and mama doesn’t want a DUI), but the short drive is also a great opportunity to question the staff for local tips. The best part: the staff can build you a private campfire on the beach, the quintessential Cannon Beach experience. They’ve got all the trimmings for s’mores, too ($79). Visit the rock, sleep like a rock, get spoiled like a rock star. From $599 per night. Stephanie Inn

Eating and Drinking in Cannon Beach

You’ve got places to see, so pick up a hot-off-the-crepe-pan breakfast at Crepe Neptune in the form of a hearty Cape Blanco (grilled chicken, pesto, tomato, spinach and cheese) or go with the sweet-and-savoury Cannon Beach (prosciutto, goat cheese, fig and honey), each $10. After some tidal pool exploration at Haystack, bring your appetite to the timber-chic Public Coast Brewing where head brewer—and longtime beekeeper, farmer, forager—Will Leroux awaits. Leroux also used to be a corporate chef, so all of that local food sourcing expertise goes right into the beer. We like the hops-till-you-drop “beast-like” Oswald IPA (74 IBU) which is also an homage to governor Oswald West, who came up with the genius idea that Oregon’s 363 miles of coastline should remain free and open to the public, a sentiment that became law in 1967 (hence, Public Coast Brewing). The menu is a family-friendly mix of farm-to-pub fare (grass-fed burgers, Tillamook cheese-topped chop-chop salads) and West Coast catches of the day, but we like the Russell Family Farms pulled pork sandwich, made from spent grain fed pork tossed with a house-made Root Beer BBQ Sauce topped with jalapeño lime cilantro slaw and chipotle crema ($13.95). Public Coast Dinner should be had at the cozy favourite restaurant-inside-a-house, the Irish Table. Pacific Northwest cuisine melds with British Isle classics for refined dishes that couldn’t be further from bland-forward North American Irish pub food: try the vegetarian wellington with earthy wild mushrooms and fresh yams baked in puff pastry and topped with truffle herbs ($25), or the seared flat-iron steak ($27) served with creamy colcannon potatoes (an Irish style mash with kale) and a rich Jameson whiskey peppercorn sauce that you’ll want to sop up with warm-from-the-oven soda bread.

Things to Do in Cannon Beach

Vancouver can be miserable during its rainy season(s), but misty winter, sizzling summer, the brisk shoulder seasons in between—it’s all good at Cannon Beach with the right windbreaker. And 100-percent public beaches mean you can (and should) buy some firewood and newspaper at the local corner store (Mariner Market stocks groceries, fish licences and Birkenstocks, too) and get a campfire sing-a-long going. Beach cruising is also really popular and Family Funcycles can hook you up with a fat-tired bike that will make zipping across the sand flats a pure joy. (Local pro tip: at night, skid your feet along the sand to light up streaks of neon-blue phosphorescence.) Shopping is pretty small-town basic in Cannon Beach (population just under 2,000), but Vintage Viaje is a wild spot for “grandmother’s attic” finds like pillbox hats with beaded netting or cream leather power blazers, but also hipster-coveted Pendleton wool plaids. There are scads of hikes and viewpoints in the area because Cannon Beach is surrounded by state parks (Ecola, Haystack Hill), but if it’s misty (which is often the case), your best bet is to drive 15 minutes south on your way out of Cannon Beach to Oswald West State Park. There are trailheads you can take that start from parking lots just off the Oregon Coast Highway, like the Short Sands Trail, which will take you to Devils Cauldron. A moderate walk through forest and coastal grass comes out at a rocky ledge that looks out onto a cliff-backed cove where the Pacific churns and splashes like crazy against sea stacks down below. Even in the fog, it’s a heart-stopping sight that’s going to make you start sweating all over with sheer delightful panic.

Your Night Out in Cannon Beach

If there are claw-tooth hammers, power saw blades and pliers on the walls, we must be at America’s quirkiest pub, the “Screw and Brew.” Officially titled the Cannon Beach Hardware and Public House, it is part hardware store and part watering hole, so you can grab your craft pint on the eclectically decorated bar side (leather airplane seats, rusty hand-saws hung up like prize game, Screw and Brew merch) and wander through the aisles of garden tools, screws (of course), paint supplies and camping gear. It closes at 10 p.m. (like most places in Cannon Beach) but you can always head across the street to the trusty old Legion if you want to keep the party going.

Pacific City

Out of the three places, this most southern beachfront town is also the most untouched by tourists. No Starbucks, no McDonald’s, no big-name hotels, just coastline, a handful of family-run businesses and a Haystack Rock that’s about 100 feet taller than Cannon Beach’s (though these aren’t the type of folk who would brag about it).

Where to Eat in Pacific City

That a town as small as Pacific City (residents totalling just over 1,000) has a craft brewery just drives home why Oregon will forever be in our hearts. Pelican Brewery and pub is right on the beach and you can saunter in—messy bun, pullover fleece, sweatpants and all—without a hint of hostess judgement. The service is warm and boisterous (can you live in a small town and not be described as a “character?”) and the food is comfort pub grub like fried-to-heck calamari, flatbreads and burgers. Wash it down with an innocuous sessional-style Pelican pint and enjoy your front-row seat to old Haystack. Pelican Brewing Well rested and refreshed, sleepy small town or no, the best breakfast diner in the Pacific Northwest awaits. We’re talking about the Grateful Bread Bakery, which is just across the Nestucca River that winds through the town. On the face of it, this unassuming spot serves up breakfast, lunch and homemade pastries, but what you don’t bargain for are the meal-sized warm and buttery-soft biscuits so divine they’ll bring tears to your eyes (slather with butter and raspberry jam), or the scrambles that make you want to fill out all the necessary paperwork to get a working visa for the cook to come back and feed you full time in Canada. They have 11 scramble adventures titled after Grateful Dead songs, but Friend of the Devil combines toothsome spicy sausage, pepperjack cheese, chilies and red peppers with cooked-to-perfection farm eggs—served with roasted potatoes and the aforementioned heavenly biscuits for $12.95. Order as many to-go biscuits and lemon raspberry scones as you can carry for the drive home or regret it forever.

What to Do in Pacific City

Sure, there’s horse riding in town (admittedly, if anywhere, these long flat beaches would be the best place for it), and the ocean means you can surf, stand-up paddleboard and kayak to your heart’s content, but the best funtivities in Pacific City are of the chillax variety. Tackling the next top-seller on your reading list on a comfy beach lounger, playing lazy games of cribbage on the deck of your Airbnb or breathing in the sea air during long walks, you guessed it, on the beach. Turn off the cell, crack a beer you picked up at (insert Oregon craft brewery here) and enjoy the simple pleasure of being miles away from responsibilities with the ever-present warmth of sunshine on your face.

Where to Stay in Pacific City

Looks like someone found out about Pacific City, because luxury accommodations have finally arrived in the form of Headlands Coastal Lodge and Spa. Headlands has 18 two- and three-bedroom condo-style oceanview cottages complete with private patios and soaker tubs, and if that’s not relaxing enough, you can head to the spa for a deep-tissue massage and follow it up with a soak in the outdoor hot tub (which obviously has an ocean view). From $570 per night for a two-bedroom cottage.

How to Get There

By Air: Vancouver to Portland flights (one hour and fifteen minutes nonstop) are about $350 round trip. By Car: Astoria, Cannon Beach and Pacific City are about a 2 hours’ drive from Portland (more if you’re stopping to buy wine...which is highly encouraged).