LGBTQ+ Travel in Southern Oregon

Home to the renowned Oregon Shakespeare Festival in Ashland and the beloved Britt Music & Arts Festival in Jacksonville, this sunny string of towns draws fans of arts and culture, outdoor recreation, farm-to-table dining, and winemaking. 

Bustling and inclusive Ashland has a walkable downtown that buzzes with LGBTQ+-welcoming restaurants, cafes, and boutiques. Here in early October, Southern Oregon Pride features several upbeat events, including a Pride Window Decorating Contest among downtown storefronts, a few different dance and burlesque parties, a drag brunch, and the always well-attended Ashland Pride Parade. 

You discover plenty of inclusive places to eat and drink in this friendly college town that’s anchored by the leafy campus of Southern Oregon University. Lesbian-owned Sammich has earned a devoted following for its gigantic sandwiches with creative fillings (try the Chicago-style Italian beef with provolone), while stylish Cocorico turns out exquisitely prepared modern Mediterranean fare in a romantic space that’s perfect for celebrating a special night out on the town. Also popular with the queer community, Hearsay Restaurant, Lounge, and Garden serves inventive contemporary American food and cocktails and is next to another exceptional Ashland performance space, the Oregon Cabaret Theatre. Other notable spots to mingle and enjoy a drink include the speakeasy-style Beaux Club and casually elegant Brickroom, which is popular for everything from coffee and lunch during the day to dinner and cocktails in the evening. 

Out in the surrounding hillside, you can spend an afternoon sampling outstanding wine at places like Belle Fiore, which often presents live music on its expansive terrace, and Paschal Winery, where you can also book an overnight in a pet-friendly cottage or glamping RV. Nearby, the charming small town of Talent is home to inclusive establishments like Legend Cider taphouse, Cafe Soleil coffee and tea house, and Ceremony: Bench & Larder, for artisan bagels and coffee. Here as well you might catch a classic play or Broadway musical at Talent’s Camelot Theatre. 

Ashland also boasts an array of romantic inns and one-of-a–kind hotels. The gay-owned Ashland Creek Inn is an inviting luxury hideaway situated beside a gurgling creek with 10 individually designed rooms, bountiful gourmet breakfasts, and a fantastic location steps from restaurants and shops. The Ashland Springs Hotel offers warmly appointed rooms in a stately 1925 downtown tower with a terrific farm-to-table restaurant, Larks. Across the street, the funky and historic Columbia Hotel has affordable rooms and art-filled common spaces, and it’s a host lodging during Southern Oregon Pride. Other appealing options within walking distance of downtown theaters and restaurants include gay-owned Arden Forest Inn, set inside an 1890s mansion and carriage house, and the Winchester Inn, which comprises two meticulously restored homes and three roomy cottages. And just 12 miles east of town on the outskirts of ruggedly beautiful Cascade-Siskiyou National Monument, lesbian-owned Willow-Witt Ranch offers relaxing accommodations and campsites on a pastoral farmstead with hiking trails and friendly alpine goats. 

The largest city in Southern Oregon, Medford has a lively downtown with several bars and craft breweries popular with LGBTQ+ folks, including The Gypsy blues bar, the Grape Street Bar, and Common Block Brewing Company, which has an additional location in Klamath Falls. Savor first-rate Italian fare at Pomodori Osteria, and be sure to see what’s on at the historic Craterian Theater at the Collier Center for the Performing Arts. The city is also home to the famous fruit and gift mail-order retailer Harry & David, which is a supporter of LGBTQ+ causes and has its own brick-and-mortar store, an excellent place to stock up on picnic supplies for a hike or a day in the wine country. Harry & David also carries the superb wines of LGBTQ winemaker Sara Garr’s Circadian Cellars label; you can also pick up bottles at Cartwright’s Market and The Beatrice Wine Bar + Kitchen, which is beloved for its drag queen bingo parties. In June, get to know the city’s sizable queer community during Medford Pride, which is enthusiastically supported by a number of area businesses, including Over Easy Southern Oregon brunch restaurant and Mochi Donut House, where you can treat yourself to gluten-free mochi donuts and waffles as well as creamy boba milk teas. 

Just outside Medford in the friendly city of Phoenix, enjoyable hangouts that draw plenty of LGBTQ+ folks include Phoenix Dripp Cafe for locally roasted coffee drinks and decadent pastries, and Clyde’s Corner to feast on sublime wood-fired pizzas with interesting toppings like bacon, brie, and pears, or roasted butternut squash with capicola salami. Farther north up the Interstate 5 corridor, pop into downtown Central Point to pick up tantalizing baked goods and fluffy biscuit sandwiches at Lou’s Loafs, and award-winning blue cheeses and other gourmet treats of LGBTQ+-owned Rogue Creamery, which also features a small cafe serving ridiculously delicious grilled cheese sandwiches.

In the outdoorsy town of Grants Pass, there’s an intimate but popular Pride festival in June and several businesses with a following in the LGBTQ+ community, including Rogue Roasters for espresso and light bites, True Juice for organic smoothies and avocado toast, and Agora for made-from-scratch breakfast and lunch fare, including festive Sunday brunches. About a half-hour drive north of town, Nomenus & Wolf Creek Sanctuary is a serene, community-oriented queer retreat created and operated by the Radical Faeries. They welcome visitors by advance arrangement.

Stretching across the sun-kissed Applegate Valley, between Grants Pass and Medford, you’ll discover some of the region’s most esteemed wineries as well as the postcard-perfect Gold Rush-era village of Jacksonville, with its restored 19th-century shopfronts. In July, the pastoral grounds of Jacksonville’s LGBTQ+-owned LongSword Vineyard are the site of Country Queer Summerfest, featuring music, drag shows, food trucks, and a silent disco. Other wineries in the area with a strong community following include DANCIN Vineyards, which also serves up tasty pizzas on its sprawling terrace, and Hummingbird Estate, where you can also spend the night in one of the romantic guest rooms in this lavishly appointed 1920s mansion. Also stop by Blossom Barn Cidery to sample the crisp and refreshing “perries,” made with pears and other fruit grown in Oregon. If you’re seeking friendly and knowledgeable guidance on the area’s wineries, consider booking an excursion with LGBTQ-owned Latitude Wine Tours, which offers private five-hour excursions to three distinct wineries, personalized to match your group’s preferences and palate. While in Jacksonville, stop by Cerebus Coffee for a perfectly crafted latte, and Violets and Cream for a scoop of ice cream or a handful of old-fashioned candies (they have a second location in Medford).