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More than 100 feet up in the air, with the wind howling and sheets of rain cascading sideways across a charcoal-colored sky, Astoria was giving us its blustery best.
We had climbed to the top of the Astoria Column to take in the sweeping views of Oregon’s oldest city and the first permanent American settlement on the West Coast. Instead, we had ascended into a squall—the kind infamous for wrecking countless ships over the years at the treacherous spot where the Columbia River and Pacific Ocean meet.
Yet even clenching the railing of the 99-year-old tower, getting pelted by the elements, it’s hard not to fall for the dramatic panorama of steep, green hills dropping abruptly into the water. There’s something to be said for a place that can look so good in such bad weather. Still, it’s nice to know it won’t last forever.
“Having grown up in Portland, I know you can have those periods when it’s gray all day long—it’s not like that here,” explains David Strom, an Astoria blogger and zine maker. “It’s a coastal climate and that wind that brought the rain can just as easily blow away the clouds and suddenly there’s the sun.”
Picturesquely perched as much over the water as by it, Astoria has long been a popular weekend getaway for Portlanders. But with its occasionally stormy weather, you might not have it high on your list of winter escape destinations.
That would be a mistake, since few places so readily embrace the darker months like Astoria does. Winter here is less a season than a state of mind.
“It never really gets boring,” says our bartender Audrey, as she mixes us two strong cocktails in huge tiki mugs at the nautically themed watering hole Dead Man’s Isle (1239 Duane St., deadmansisle.com). “There’s always something to do in town, or you just suit up and head to the beach.”
It’s true: Just as much of the Oregon Coast is heading into winter hibernation, the hardy denizens of Astoria are either getting outside or gearing up for some of the biggest events of the year. The following tips should help you experience the city like a local.
February is especially jam packed, with both Fort George’s Festival of Dark Arts and the Fisher Poets Gathering taking place each year. The former, a popular celebration of dark beer along with live music and art installations, is now in its 13th year, while the latter has brought together poets with ties to the fishing industry to Astoria for even longer.
Those two events have made the month one of the busiest times to visit. Brian Bovenizer, marketing director for the Fort George Brewery, cautions tickets to the 3,000-visitor festival go extremely fast when they go on sale at dawn on Black Friday after Thanksgiving.
“It’s sold out in less than four minutes the last two years,” he says. “But we do stout for the entire month. We keep the arcade there for the whole month.”
Take it outside
Keeping very on brand for Astoria, much of the Festival of Dark Arts takes place outdoors regardless of the weather.
“We shut down the street and then each pub becomes a pouring location, but a lot of that is outside: There’s a stage outside, there are food trucks outside, a big tap trailer outside,” Bovenizer says.
There was one festival performer, however, who didn’t care for the February chill. “I had a snake charmer, but then they realized it was going to be 40 degrees, and the snake didn’t like that,” he admits. “But the fire dancing is always a hit.”
When he’s not at the brewery or playing in his local band The New Old Stock, Bovenizer is also heading outside to catch some waves: “The winters here are great for surfing. That has been a huge thing for me.”
Of course, Fort George doesn’t just pour its energy into the festival—it offers seasonally appropriate activities all winter long. For example, the brewery hosts Thursday talks from October through May on a broad range of topics, from the Seaside riots (when roving mobs of rowdy youths made a Labor Day tradition of getting into trouble in the coastal town from 1962 to 1964) to the implications of artificial intelligence.
“I had never even heard about those riots before that,” says Strom, who eventually moved to Astoria after first discovering it with his future wife more than 17 years ago.
“I was a TriMet warrior in Portland, so I immediately loved the walkability of it all here,” he says. “We can see the bridge and river from our home, which is amazing.”
Once Strom relocated permanently, his blog Dave Knows Portland became Astoria Dave (astoriadave.com). But having worked for years in the software industry, his latest project is the decidedly analog zine Astoria Man: “I didn’t want to feed the AI scrapers anymore.”
The cover of the first edition is fittingly emblazoned with the Astoria Column (1 Coxcomb Drive, astoriacolumn.org). Inside, you’ll find art, information about ship horn signals and some history about a century of local phallic jokes made about the column, aka “Astor’s Shaft.”
Hang with the locals
Though his focus is no longer on the digital world, Strom’s blog still has some useful links for finding things to do and places to go in Astoria. One great resource is Ophelia (astoria-events.com), a calendar of events and happenings open to the public. From wood carving classes to a tour of the city’s underground tunnels, there are lots of fun opportunities to hang with the locals.
Another popular activity is roller skating from 5 to 8 pm on Fridays and Saturdays at the former Astoria Armory, which is now a community center and event space. Rentals are available if you forgot your skates.
Strom also suggests checking out Galactix (254 9th St., subterranean level, 831-772-2349, thegalactix.com), an underground arcade styled as an “interstellar cruiser” for an immersive sci-fi experience. Just be prepared to download an app to pay for the games—which can be somewhat tricky after pounding several cocktails at Dead Man’s Isle. Fortunately, there is a very friendly guy at the counter offering some interstellar help.
Walk the river
Locals probably don’t stroll down the entire length of the Astoria Riverwalk very often, but it’s worth a ramble, if only to gawk at the awkwardly large container ships moving slowly up or down the Columbia, as well as to watch the sea lions bark at each other as they jockey for the optimal napping position underneath the pier. Stretching some six miles along the waterfront, the Riverwalk includes viewpoints and historical information along the way. If you’re ever feeling tired, hop on the old-fashioned trolley that runs the entire distance for $1.
After a tasty pastry and coffee at either Blue Scorcher Bakery & Café or the Astoria Coffee House & Bistro, you can check out the nearby Columbia River Maritime Museum (1792 Marine Drive, 503-325-2323, crmm.org). Currently undergoing renovations and a massive expansion slated to finish in 2026, the museum is still worth a visit to get a better idea of Astoria’s seafaring past and present.
Part of what makes this city of 10,000 special is that it still retains some of its working-town vibe despite catering to tourists. Though canneries may have given over to craft brewers and coffee shops, Astoria remains headquarters to the Columbia River bar pilots—those skilled mariners who guide the giant container ships through some of the most dangerous waters in the world—and home to a small commercial fishing fleet.
New exhibits at the museum include a collaboration with the Chinook Nation exploring Indigenous maritime traditions established long before John Jacob Astor helped fund the settlement of the region as part of his fur-trading empire. Also be sure to go aboard the decommissioned lightship Columbia moored outside, since it’s included in your admission.
Find your fish
Speaking of boats and fish, it’d be a shame not to enjoy some of the quality seafood to be found around town. Not far from the museum you can grab fish and chips from Bowpicker—an actual boat converted into an on-land kitchen. There is minimal outdoor seating, but that doesn’t bother the locals. A good indoor option is the South Bay Wild Fish House (262 9th St., 503-741-3000, southbaywild.net), which is connected to a boat still in the water, the small family-owned commercial fishing vessel of the same name.
Once you’ve had your fill of seafood, it’s probably time to wander a bit. Soft serve at the nearby Custard King is always a good idea. If you need your Goonies fix, you can join fans making a pilgrimage to the actual house made famous by the movie, but there’s actually more to see downtown at the Oregon Film Museum (732 Duane St., 503-325-2203, astoriamuseums.org/explore/oregon-film-museum).
A magic getaway
Otherwise, Astoria’s main drag consists of an intriguing assortment of shops and businesses, from a seemingly well-stocked pawn shop to a knitting yarn store, and even one magic shop.
The owner, Seth Howard, is a professional magician whose greatest disappearing act was possibly leaving Portland for Astoria 11 years ago. At first, he managed the local Goodwill store. But after the pandemic, his wife encouraged him to open The Magic Shop & More (1125 Commercial St., 503-741-3047, themagicshopandmore.com). Now, when he’s not doing tricks for customers during the day, Howard performs magic shows around town two nights a week.
Having fled Portland, Howard says he’s content spending the colder months of the year in Astoria. “You know, the winter in the city can be kind of drab, whereas here it’s gorgeous,” he explains. “I don’t need to get away from my getaway.”
Where to stay
Unless you happen to know someone in town, you’re probably not going to stay in Astoria like a local. But that’s OK because you can at least replicate their vistas of the Columbia at lots of different types of accommodation. If you’ve got money to spend, the boutique Bowline Hotel has sleek rooms right on the edge of the pier with fantastic river views and outdoor Finnish barrel saunas. Be prepared for the occasional sea lion argument during the night, however. The Cannery Pier Hotel & Spa is another high-end spot on the water, but you can also head down a bit farther for the more affordable if somewhat dated Astoria Riverwalk Inn. There are also plenty of options right in downtown, such as the Commodore, Norblad and supposedly haunted Hotel Elliott.
Getting there
There are two routes from Portland to Astoria, and both are roughly two hours by car. You can either take Highway 30 north of downtown heading west—essentially following the Columbia all the way to the ocean—or you can drive Highway 26 west past Beaverton to the coast, where you’ll take Route 101 north until you reach Astoria. There is, however, a bus for all the TriMet warriors out there: From Union Station it will take you about three hours to reach the Astoria Transit Center, which is smack dab in the middle of the city’s extremely walkable urban core. There are two buses a day, and fares range from $3.50 to $18 one way depending on how far in advance you book (oregon-point.com).
Oregon Winter is Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, November 21, 2025. Find your free copy at one of the locations noted here, before they all get picked up.
