6 Romantic Small Towns in Oregon

January 26, 2017 (Updated February 3, 2017)

What is it about Haystack Rock that inspires endless gazing from a beachfront balcony? Or the glittering sight of snowy Mt. Hood, from the window of a rustic lodge?

They’re Oregon icons that are made for romance, to be sure. Whether it’s glorious trails for trekking, cozy nooks for relaxing or charming downtowns for dining, here’s where to head this Valentine’s Day and beyond for some classic Oregon romance:

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Joseph, for wild and scenic beauty

If you don’t swoon over the fine art galleries, handmade chocolates and coffee roasters packed into the uncrowded Eastern Oregon town of Joseph, you’ll surely get weak in the knees at the sight of the Eagle Cap Wilderness — Oregon’s largest wilderness area. Wanderlust adventurers will find hundreds of miles of trails here and around Wallowa Lake, in Joseph’s backyard. Some of the drives and hikes are steep and dangerous, so check conditions and know your limits. There are plenty of incredible but gentler vistas to take in — try Chief Joseph Trail at the Wallowa Lake Trailhead, where you’ll walk through an alpine forest with views of the lake, wildlife like mountain goats, mule deer and elk, and a waterfall called BC Falls, which you won’t find on many maps. Settle in at one of the eight year-round cabins at the plush Wallowa Lake Lodge, steps from the lakefront, or soak up the 360-degree view at the pet-friendly Creekside Country Haven Bed and Breakfast on 20 secluded acres just outside of Joseph.

Government Camp, for chilling at the mountain

This verdant outpost, at the western face of Mt. Hood, is made for memories — not just for kids, but grownups too. Skip the kiddie hill and take up a new winter snow sport together at Mt. Hood Skibowl, Summit Ski Area, Timberline Lodge or Mt. Hood Meadows. Or take a thrill ride on Skibowl’s three-story, 800-foot-long cosmic zip line adventure, a surreal spectacle with colorful laser lights flashing across the bright snow. Stay at a cozy rental or live it up at Timberline Lodge, where tempting winter deals await. One package offers lodging with an hour-long scenic snowcat ride, plus a wine and cheese platter. Another includes a guided snowshoe stroll around the lodge by moonlight with a Forest Service ranger. And another includes dinner in the elegant Cascade Dining Room with a midweek stay.

Cannon Beach, for beachy vibes

Salt air and walks on the beach by day, sunsets and bonfires by night. A beach getaway in Cannon Beach is a classic retreat, with all the conveniences of home and then some. Indulge in white tablecloth French Italian cuisine, such as duck breast with braised greens, foie gras and truffle oil, at Newmans at 988, a tiny house-turned restaurant celebrating its 11th anniversary in February 2018. Or stock up with gourmet fixings for a picnic or night in at Provisions 124 and The Wine Shack. Stay at the oceanfront Stephanie Inn for boutique luxury and stunning views. Or pamper yourself with an oversized claw-foot tub, four-poster bed at the New England-style Cannon Beach Hotel, built in 1914 and since refurbished, one of the last historic lodgings on the Oregon Coast.

Carlton, for wine lovers

From the organic pinot noir, pinot gris and chardonnay at Omero Cellars (based in Newberg) to the warmer-climate reds at Troon Vineyard (based in the Applegate Valley of Southern Oregon), the little farm town of Carlton is — in the heart of the Willamette Valley — is a showcase for the best of Oregon’s wines. With 40 wineries, 22 wine tasting rooms and an ample dining scene to match, long meals and uninterrupted face time are the norm here. Enjoy a juicy rib-eye and pommes frites at French bistro Cuvee, or a satisfying Carlton Farms smoked ham sandwich at The Horse Radish, which also offers live music Friday and Saturday evenings. A short walk from downtown, take a bottle back to your room and wood-burning fireplace at the Carlton Inn B&B or the modern Carlton Pinot House.

Sisters, for a tasty backcountry adventure

Bundle up for an enchanting time at Hoodoo Ski Area, where you’ll have a blast working up a sweat on a beginner-friendly cross-country ski trail. Head into evening in downtown Sisters with an artisan cocktail and mushroom risotto at Latigo Restaurant and then a nightcap with live music and dessert at the The Open Door Wine and Art wine bar. Cap your day with a cabin stay at the woodsy Metolius River Lodges or the uber-romantic FivePine Lodge, with various suite options and an on-site spa. Spend the next day at the much-buzzed-about The Suttle Lodge, where you can take an easy stroll around the 3.2-mile Suttle Lake as it winds through the forest. Unwind at The Boathouse, overlooking the lake, with a bloody mary and fresh potato chip-crusted trout fish n’ chips or bowl of steaming chowder, prepared with local salmon and lake trout.

Jacksonville, for arts and culture

Artisan producers, shops and bistros — not to mention some of the region’s best wine tasting — abound in Jacksonville, an out-of-the-way Southern Oregon town that’s steeped in historic charm and artsy culture. Explore some of the 20 miles of urban green space at Woodland Trails, right in town, or take a 15-minute drive north to Table Rocks, two mesas with panoramic views, accessible via a 2-hour hike. Later in the day, unwind with a couple’s treatment at Angelica Day Spa, which offers an infrared sauna — a welcome antidote to blustery winter days. Upscale dining options in the walkable downtown include Gogi’s Restaurant and C St Bistro, where you might find braised lamb shank or pork belly confit on the seasonally rotating menu, both with extensive wine, beer and cocktail lists. Overnight options include the Magnolia Inn, the TouVelle House Bed and Breakfast and the Jacksonville Inn.

About The
Author

Jen Anderson
Jen Anderson writes and edits Travel Oregon’s e-newsletters and other online content. She loves finding the latest places to eat, drink and play around the state with her husband and two young boys. Brewpubs, beaches and bike trails top the list.

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Ask Oregon

Where should we stay for a romantic coastal getaway?

On the North Oregon Coast, Stephanie Inn in Cannon Beach is one of the coast’s most luxurious lodging options. Cannon Beach offers quick access to scenic areas including miles of sandy beach, Oregon’s iconic Haystack Rock and beautiful Ecola State Park. For a runner-up, the views of Cannon Beach and Haystack Rock can’t be beat…

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