6 Romantic Small Towns in Oregon

January 26, 2017 (Updated February 20, 2019)

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 romantic Oregon icons in every sense of the word. Whether it’s glorious trails for trekking, cozy nooks for relaxing or charming downtowns for dining, here are six of Oregon’s most scenic small towns for couple’s getaways.

Government Camp, on the western face of Mt. Hood, is made for making memories. (Photo credit: MoscaStudio.com)
A stay in Cannon Beach is a classic retreat, with salt air and walks on the beach by day, sunsets and bonfires by night. (Photo credit: Nicke Bournias)

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 SkibowlSummit 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 a guided snowshoe stroll around the lodge by moonlight with a Forest Service ranger. 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 small house-turned restaurant that celebrated its 12th anniversary in February 2019. 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, it’s 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), Carlton is a showcase for the best of Oregon’s wines. In the heart of the Willamette Valley, this little town claims 40 wineries, 22 wine tasting rooms and an ample dining scene to match. Enjoy a juicy rib-eye and pommes frites at French bistro Cuvée, or a satisfying Carlton Farms smoked ham sandwich at The Horse Radish, which also offers live music Friday and Saturday evenings. Take a bottle back to your room and wood-burning fireplace at the Carlton Inn B&B or the modern Carlton Pinot House, both centrally located for your next vino adventure.

Cap a day at the slopes with the uber-romantic FivePine Lodge in Sisters. (Photo credit: FivePine Lodge)
You’ll surely get weak in the knees at the sight of the Eagle Cap Wilderness outside Joseph.
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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. In the evening, head to downtown Sisters for pinot noir and bacon-wrapped meatloaf at The Porch and then a nightcap with live music and dessert at The Open Door Wine and Art. 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 on a 3.2-mile trail around Suttle Lake. 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.

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 or the dog-friendly Barking Mad Farm B&B, a working farm that serves a hearty farm-to-table breakfast.

Jacksonville, for arts and culture

Artisan producers, shops and bistros — not to mention some of the region’s best wine tasting — abound in Jacksonville, a 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.