Oregon’s popularity as an LGBTQ destination undoubtedly starts with Portland, a bona fide hotbed of queer activism, arts and culture. But I’ve long been surprised by how many other communities around the state have vibrant queer scenes. My partner and I have been to every county in Oregon — we’ve hung out with locals at small-town Pride festivals, mingled with kindred spirits in bars and brewpubs both in progressive college towns and remote hamlets, and discovered many gay-owned or highly welcoming inns along the way. Here are some of my favorite places around the state for enjoying a memorable weekend with my partner, from rugged mountain towns with access to amazing hiking to arts-inflected urban oases with fun nightlife, shopping and cool cafe culture.
Planning for Pride? Check out this local’s guide to Pride festivities in Portland as well as other queer-friendly cities around the state.
With one of the largest concentrations of LGBTQ residents in the country, Portland is a queer epicenter on the West Coast, with a slew of thumpin’ bars and dance clubs (hosting popular dance nights like Cake) and dozens of community-owned businesses, like the queer-feminist clothier Wildfang. Great times to visit include the Portland Pride Festival in mid-June and Latinx Gay Pride in July. On the city’s east side, LGBTQ culture thrives in pedestrian-friendly neighborhoods like Hawthorne, Mississippi and Alberta. Countless hotels in Portland enthusiastically welcome the LGBTQ community, and you’ll also find a number of queer-owned or managed accommodations, most of them on the East Side. Consider the retro-chic Jupiter Hotel and the newer and fancier Jupiter Next across the street, both of which cater to queer travelers. Other gay faves in this part of town include lesbian-owned Tiny Digs, which is made up of eight cute and cozy tiny houses, and the Lion and the Rose and Portland’s White House, two stately, queer-owned bed-and-breakfasts in the historic Irvington neighborhood. For a more rural setting, book one of 10 rooms or a separate guest cottage at the lesbian-owned Scappoose Creek Inn, a beautiful farm situated just outside of Portland near Sauvie Island and the Columbia River.
Eugene and the South Willamette Valley
Oregon’s third-largest city, progressive Eugene is home to University of Oregon (and its related, excellent museums) and one of the coolest, queerest little neighborhoods in the state, Whiteaker, where you can stroll and people-watch amid such inviting hangouts as Izakaya Meiji and Sam Bond’s Garage. Beer lovers should also check out Hop Valley Brewing, which produces Reveal Pale Ale, a portion of whose proceeds support LGBTQ nonprofits. The city’s queer community hosts a well-attended Gay Pride in August, and in downtown Eugene you’ll find a slew of bars and clubs that have a mixed following as well as a dedicated queer establishment, Spectrum Eugene, which opened in fall 2018. It’s a short walk from the lively Market District, with its many superb restaurants and shops. Close to the U of O campus, the LGBTQ-inviting Excelsior Inn has 14 smartly designed rooms; rates include a lavish full breakfast. Eugene lies at the southern end of the famed Willamette Valley wine country — there are several stellar tasting rooms within a short drive of the city, including dramatically situated King Estate. If you want to spend the night amid rolling vineyards, you’ll find plenty of lodging options throughout the valley. Farther north, try the gay-owned Dundee Manor, a romantic Edwardian estate that’s a short hop from dozens of internationally acclaimed wineries, including Argyle, Domaine Drouhin and Sokol Blosser.
The terminus of the Lewis and Clark expedition and a historic maritime city, Astoria enjoys a storied setting close to Oregon’s eye-popping coastal scenery, right at the mouth of the mighty Columbia River, which you can admire from a scenic paved and boardwalk river trail. Today this compact, hilly metropolis — known to many as the film location of “The Goonies” — is sometimes described as a miniature San Francisco, with its diverse nightlife, indie-spirited galleries and shops, and Victorian vibe. The relatively young Astoria Pride gathering each June receives tremendous support from local businesses that are well worth visiting any time of year, among them Fort George Brewery + Public House, Buoy Beer Company, Frite & Scoop, Coffee Girl and the handsomely restored Liberty Theatre. And gay-owned Astoria Coffeehouse & Bistro is a must for breakfast, coffee, cocktails or dinner. You’ll find no shortage of charming queer-friendly hotels, including a pair of hip boutique properties set in historic downtown buildings: the Commodore Hotel — which is also home to the convivial Street Fourteen Cafe— and the funky Norblad Hotel, one of the region’s best values. For smashing river views and some of the cushiest digs in town, book a room at the Cannery Pier Hotel & Spa. Tip for solitude seekers: It’s not unusual for hotels to be fully booked in summer, particularly during July and August. For the most relaxing trip, plan a mid-week visit between October and May.
Crater Lake and the Umpqua National Forest
For a romantic wilderness adventure where nightlife consists of gazing at brilliant starry skies, consider venturing into Southern Oregon’s nearly million-acre Umpqua National Forest, an area renowned for hiking, fly-fishing, rafting and countless other outdoor activities. A bit of a distance from any sizable towns, the region is home to some magical overnight roosts. At gay-owned Summit Prairie Fire Lookout, accommodations are in a spacious suite set atop a 40-foot fire tower whose wraparound deck (with its own outdoor shower) offers dazzling views of the tranquil countryside. Set in tiny Tiller along the South Umpqua River, it’s a 90-minute scenic drive from the main entrance of Crater Lake National Park, which is itself an iconic getaway — the historic Crater Lake Lodge is a memorable place to spend a night or two. A rustic but affordable option on the Rogue-Umpqua Scenic Byway, about an hour from Crater Lake’s summer-only northern entrance, Umpqua’s Last Resort is a gay-owned RV park and campground with well-equipped cabins as well as primitive campsites; it hosts LGBTQ gatherings throughout the year. This part of the state is also near Nomenus & Wolf Creek Sanctuary — a 30-minute drive from Grants Pass — a peaceful retreat created and operated by the Radical Faeries.
Home to the celebrated Oregon Shakespeare Festival as well as Southern Oregon University, this vibrant city is a favorite getaway for culture seekers, foodies and outdoor enthusiasts. Downtown abounds with lively restaurants and bars, and the city is host to Rogue Valley Pride, set right in downtown’s picturesque Lithia Park each October. Standing Stone Brewing Company, which participates in Pride, serves tasty food and beer, and Case Coffee Roasters is a cheerful spot to fuel up in the morning. For a romantic dinner, head to Larks Home Kitchen Cuisine, which is justly known for its farm-to-table cuisine and impressive wine list, and is inside the upscale, LGBTQ-friendly Ashland Springs Hotel. If you’re in town to attend the theater, consider queer-popular Arden Forest Inn, whose smartly appointed rooms occupy an 1890s mansion and carriage house a short walk from the theater. For a more pastoral experience, stay at lesbian-owned Willow-Witt Ranch, just 12 miles east of Ashland. With accommodations ranging from an upscale guesthouse to affordable wall tents and primitive campsites, this rambling property offers guests the chance to gather eggs, tour the farm and hike with the friendly pack goats.
Bend and Central Oregon
The cultural and recreational hub of Central Oregon, bustling Bend makes a terrific base for outdoor adventures. Skiers and snowboarders can hit the sunny slopes of Mt. Bachelor, which hosts an annual LGBTQ Ski Weekend in late January/early February. And throughout the year there’s fantastic hiking nearby among the craggy cliffs of Smith Rock State Park and the otherworldly geological formations of Newberry National Volcanic Monument. The setting of Central Oregon Pride each year in late June, downtown Bend is a picturesque high-desert city that’s bisected by the scenic Deschutes River and abounds with noteworthy craft breweries, third-wave coffeehouses and farm-to-table eateries. Offbeat McMenamins Old St. Francis School and the eco-chic and contemporary Oxford Hotel are great places to stay, especially if you wish to be within walking distance of local brewpubs. For a small-town getaway closer to the natural wonders of the Cascades Range, the romantic and LGBTQ-welcoming FivePine Lodge & Spa is a gorgeous pine-shaded compound of Craftsman-style cabins that are ideal for a quiet getaway.
Hood River and the Columbia River Gorge
A friendly yet sophisticated little town with an increasingly visible LGBTQ community, Hood River launched its first Pride celebration in 2017 (it’s held in late June) and makes a charming getaway for touring wineries and orchards, hiking in the breathtaking Columbia River Gorge or playing amid the snowcapped slopes of nearby Mt. Hood. On your way out here from Portland, stop to sunbathe amid throngs of LGBTQ folks on the banks of the Columbia River at clothing-optional Rooster Rock State Park. In downtown Hood River, check out queer-popular eateries like Solstice pizzeria and Broder Øst — the latter is inside the historic Hood River Hotel, an atmospheric and reasonably priced downtown property that’s steps from such inclusive nightspots as Whiskey Tango and River City Saloon. About 15 miles south on the main road to Mt. Hood, and close to many orchards and U-pick farm stands, the intimate and beautifully appointed Old Parkdale Inn is a lovely, gay-friendly B&B that’s ideal if you’d prefer a quieter, more countrified setting.
Famed for the Pendleton Round-Up rodeo, this down-home town at the base of the Blue Mountains in Eastern Oregon is a hub of wild-west culture. Highlights include the outstanding exhibits on Native American heritage at the Tamástslikt Cultural Institute, and Pendleton Woolen Mills, the historic blanket production facility of this famed woolen mill. Pendleton also makes a perfect gateway for exploring the spectacular Wallowa Mountains farther east. Opposite the Umatilla River from downtown, the queer-owned Pendleton House B&B occupies an elegant 1917 Italian Renaissance-style mansion with six over-the-top sumptuous guest rooms. If you’re up for venturing farther into the gorgeous Eastern Oregon region, consider spending a night or two at the cozy Barking Mad Farm B&B in Enterprise, which is an ideal base for hiking and boating, or at the elegant and historic Geiser Grand Hotel, a turreted grande dame set amid shops and eateries in the former gold-mining hub of Baker City. Both of these gay-welcoming properties exude charm.