Founded in 1811, this compact seaside town can feel closer to the five-century-old urban settlement of Portland, Maine, than to Portland, Oregon. Simultaneously a young, thriving, mini-metropolis and an antiques-laden museum row, Astoria can leave a visitor wondering if they should move there to be both part of its exciting future and a steward of its fascinating past.

You might pass a hilltop house for sale and jump ahead a few decades imagining a peaceful retirement: sipping locally roasted coffee and gazing out at the Columbia River bar and Pacific Ocean before your shift as a volunteer motorman (the term is gender neutral, apparently) pointing out the fishing town's repurposed canneries from the Astoria Riverfront Trolley; a friendly hiker helping others navigate the wooden walkways and tree-root stairs of the Cathedral Tree Trail, en route to the hilltop Astoria Column to throw a balsa-wood plane off its observation deck; an educator at the Columbia River Maritime Museum, home to a 44-foot Coast Guard lifeboat perched midrescue on a 20-foot wave; or a chatty fan at the Oregon Film Museum, telling future generations about the wonders of Astoria-filmed Short Circuit, Free Willy, Kindergarten Cop, Teenage Mutant Ninja Turtles III, and The Goonies.

But we're getting ahead of ourselves. This is, after all, a vacation guide, not a retirement planner! Under two hours away, Astoria is day-trip distance from Portland but is so packed with things to do (and beers to drink) that an overnight or a weekend getaway is advised. Enjoy urban chic on the cheap with a Euro-style cabin room (or spend more for your own bathroom) at the Norblad or the Commodore. Both mod boutique hotels are steps from the colossal Fort George Brewery, which slings pub food on the ground floor and pizza upstairs. (Standard bearer City of Dreams Pale Ale, hazy new favorite Magnetic Fields, and smaller-batch IPAs like Fanzine are usually on tap on both levels.) For Jazz Age grandeur, book a room at the century-old Hotel Elliott, renovated in 2003 with historical preservation in mind. For a lavish spa experience in an unbelievable setting, opt for Cannery Pier Hotel, set on piers 600 feet out into the river, under the soaring Astoria-Megler Bridge.

And by day? Play, wander, and eat. Situated in a grounded boat right in town, the Bowpicker offers a classic fish-and-chips plate (and a storied wait for your order) that's become an Oregon rite of passage. If the crowd and the trash-can-swarming insects are a bother, though, head for the Ship Out cart on the south side of Youngs Bay for a properly chunky chowder and pillow-light fried cod, halibut, and more, the breading bubbly and nearly translucent, with a dill-forward tartar sauce, fennel slaw, and solid fry sauce. If Ship Out’s breaded fries aren’t your style, grab a simpler version at the downtown waterfront at Frites & Scoop, and throw the house-made ice cream, too, which comes in flavors like Foggy Lemon (with Earl Grey custard) and Coffee Toffee.  

Families will want to block out time for Tapiola Park and its castle play structure, which includes a climbing wall painted like a shipwreck. Downtown, shop for vintage threads at Garbo's, Nordic kitchen gear at Finn Ware, and, um, human-wax-figure candles with wicks in unexpected places at the Weird Sisters Freak Boutique.

Top photo of the Astoria-Megler Bridge courtesy Dale Nibbe