Stop 1: Gearhart

The cottages at Gearhart Ocean Inn are clean, breezy, and two blocks from the sea. McMenamins Gearhart Hotel is just a jig north, sandwiched by Del Rey Beach and the Gearhart Golf Links. A few minutes south of town, Seaside Brewing Co dishes up Dungeness crab melts and oyster shooters. Or make your bunk 25 minutes north, tucked into Oregon’s most northwesterly corner, where the cabins, yurts, and campsites at Fort Stevens State Park are just a short walk from playgrounds, old gun batteries, and the shipwrecked Peter Iredale. For dinner, fry up your own catch, perhaps caught right from the floating docks at Coffenbury Lake.

Stop 2: Manzanita

A block from the beach, rooms at the upscale Inn at Manzanita come with fireplaces, hot tubs, and private decks. Fuel up with scratch pastries and artisan sandwiches at nearby Bread and Ocean bakery—or head inland two miles to Nehalem, where Buttercup whips up rotating ice creams and equally buttery chowders. Budget travelers can book campsites and yurts at nearby Nehalem Bay State Park; celebrate those savings 15 miles north at year-old Public Coast Brewing Co and Cannon Beach Distillery (makers of award-winning rums).

Stop 3: Pacific City

This fall, the owners of Pelican Brewing plan to open a brand-new hotel right at the foot of Pacific City’s Haystack Rock. The Headlands Coastal Lodge & Spa promises a focus on the great outdoors—and soaking tubs. Eleven miles north, Cape Lookout State Park’s cabins, campsites, and yurts enjoy prime beach access to the south of Netarts Bay. (Your neighbors are Nevør Shellfish Farms and Jacobsen Salt Co.) Six miles up the bay in the town of Netarts, the Schooner Restaurant and Lounge offers quality surf and turf, along with a boat launch for kayaking and crabbing. 

Stop 4: Yachats

A beach trail wends right below the private balconies at Yachats’s cozy Fireside Motel. (Do spring for an ocean-view room.) A mile south on the town’s main drag, the fare at quirky Yachats Brewing and Farmstore is next-level homestead: beer-brined chops, tangy sourdough, house-fermented veg. For white-linen dining by candlelight, the Whale Cove Inn’s nationally-acclaimed Restaurant Beck is 35 miles north in Depoe Bay. If romance is the plan, consider extending your trip south of Yachats at Heceta Head Lighthouse—the historic light keeper’s house now operates as a bed-and-breakfast.

Stop 5: Port Orford

Nestled in a hillside grove of towering firs overlooking the Pacific, WildSpring Guest Habitat’s five deluxe cabins are luxury wrapped in wilderness. Yet you’re right on the outskirts of wind-scrubbed Port Orford—within walking distance of both chic dining at Redfish and The Crazy Norwegian’s Fish and Chips. Try out the luxe beach house of your dreams 14 miles north at Floras Lake House B&B, open seasonally through the end of September. Communal meals here may come with introductions to summering locals—and maybe an invitation to hit the lake for kayaking or windsurfing.