Ashland Pride, Wine, and the Magic of Southern Oregon

I didn’t know what to expect when I landed in Southern Oregon after a cross-country trek from Fort Lauderdale. I’d heard my destination of Ashland in Southern Oregon was beautiful—mountains, vineyards, theater, and a downtown that feels like an artist’s sketchbook. But nothing prepared me for how quickly Ashland wrapped its arms around me and said, “Welcome home.”

Where to Stay in Ashland

The moment I checked into the Ashland Creek Inn, I felt it—this odd combination of serenity and delight that only happens when a destination knows exactly who it is. The inn is gay-owned (Graham is amazing!) tucked beside a creek that lulls you to sleep at night and murmurs you awake each morning, and each suite is its own world. I am sure everyone in the building heard me exclaim, “Are you fucking kidding me?” No, it was not Shangrila, but it was the Marrakesh Suite.

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Decorated with actual items hand-picked by Ashalnd Creek Inn owner Graham Sheldon while traveling in Morocco, the room, excuse me, suite was truly a paradise away from home. A private deck, magnificent historic wood features, fireplace, kitchen, a bay of crank-open windows that let you listen to the Ashland Creek that ran through the property.

Fresh-baked sweet goodies were delivered every day to your room and breakfasts, well each day all the guests were served in the dining room at 9 AM a morning surprise that tasted like someone’s culinary love letter a new destinations across the world. A new fruit place, a new smoothie, and a new entrée most likely inspired by one of Graham’s personal journeys. And Graham himself is quite easy on the eyes. 

More Than Quaint

The Ashland Creek Inn is not even a 4-minute walk to the center of Ashland. A couple of my strolls to its main street, I would see deer laying in a field. And, yes, when I reached the center of town, I did want to twirl around like Belle and sing, “Little town, little peaceful village”, as that was the feeling that came over me.  

Make sure to spend some time going into the shops and chatting with the people as they are just as valuable and unique as the goods they are selling. It’s a small town so the shops do shutter early in the evening, the restaurants stay open a little later.

Ashland Does Pride

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And I arrived just in time for Southern Oregon Pride, which meant the whole town was rainbow-fied. On First Friday, I wandered through Ashland’s art walk, ducking into galleries where local artists showed off their talents, one store was celebrating the building’s birthday with cake and chocolates. Later, the upstairs lobby area at the Columbia Hotel transformed into a glitter-soaked playground for Seduction—Pride After Dark. Drag, burlesque, lights, heat. Solaria Flare and her cast lit up the night with a kind of joy that doesn’t ask permission, but does want to know your name. 

The next morning brought the Southern Oregon Pride Parade, a celebration that felt intimate and heartfelt in the way smaller Prides often do. The Grand Marshal of the pride parade was the new school district superintendent. Lithia Park’s Butler Bandshell hosted vendors, drag shows, and a DJ pumping music.

Ashland’s Pride is personal—where you don’t just watch the parade, you feel it. I was an outsider watching, but soon became a local as everyone was just so epically open with light and love and respect. Not sure I’ve seen a happier pride. 

Outdoor Markets and Parks

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Wandered downtown, sipping chai tea, browsing queer-friendly shops, I also slipped into the Rogue Valley Growers & Crafters Market. It wasn’t pretentious or oversized—just farmers, florists, and artisans genuinely excited to share their corner of Southern Oregon.

Look and you’ll get sucked in and visit every booth, start a conversation with each vendor, and then order something to be shipped back across the country. Guilty.

Don’t Forget to Look Up

While strolling downtown, I would get distracted by, not something shiny, but something big and grand behind the cute buildings that lined the streets. The hills and mountains that framed the cityscape reminded me that more nature was just a step away.  And that is one main reason people love Southern Oregon, the access to nature.

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When I needed nature, Ashland delivered. Lithia Park, with its fall color show, led me straight into the Ashland Creek Watershed, where trails wind from woodland shade to sweeping mountain views. Hiking here feels like stepping into a watercolor painting. Pilot Rock, Grizzly Peak, and White Rabbit Trail all teased me with options—but even the simple loop around Lithia Park felt like a recalibration of my brain.

And Then the Wine Happened

One of the highlights of my visit was a full-day tour of the Applegate Valley with Latitude Wine Tours, an LGBTQ-owned company that treats wine tasting like a curated conversation rather than a checklist. My guide, Faith—WSET Level III and packed with charm—introduced me to the region’s wineries with an educator’s insight and a friend’s warmth.

We tasted at Long Walk, then at Circadian Cellars, an LGBTQ-owned business where its wines felt personal, almost intimate.

Circadian Cellars chooses unique vineyard sites from across the Rogue Valley, Oregon to create small batch wines. Our goal is to highlight the varietals that grow in the diverse climate of Southern Oregon and provide a new vantage point as envisioned by Chief Cellar Rat, Sara Garr.

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Sara, you’ll be getting an order from us soon now that we are home! One of each and two Primitivos!

Lunch at Sammich, also LGBTQ-owned, proved Ashland’s queer community runs deep—and runs delicious. Their sandwiches are decadent, messy in the best way, and absolutely worth the hype.

Pleasing Food Options

Ashland’s dining scene kept surprising me: Filipino comfort food at Harana Café, the refined coziness of Alchemy, the speakeasy seduction of Hearsay, and locally loved staples like Brickroom, which became both a Pride hangout and a late-night dance stop on multiple nights. We also kept it simple and tasty at Umami and Skout Brewery. Each spot offered a different window into Ashland’s character—artsy, welcoming, a little quirky, and very proud. And who can pass up a late night ice cream from Zoey’s.

Comfy Cozy Acceptance

One of the most beautiful things about traveling as a gay man is finding places where I can just… exist. Ashland wasn’t trying too hard, and that was the charm. The Pride flags weren’t performative—they were lived-in. The queer-owned businesses weren’t novelties—they were part of the fabric of the town.

About That Superintendent

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Should we start off with Superintendent Dr. Joseph Hattrick being on the Kelly Clarkson show?  Yes, let’s.

We talked to Joseph about one of his first duties as a new Superintendent, to tell the town that they had this massive economic hardship that may mean school closures, firing of educators and staff, and canceled school days. His appearance on the Kelly Clarkson show summed that whole fiasco up nicely.

But why Ashland? a town of 21,000 people in the middle of Southern Oregon, it doesn’t sound like it would be accepting. It was a sundown town until World War II, but now it is home to Southern Oregon University. 

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Josep Hattrick grew up in Vancouver, Washington, a city not as progressive as its neighbor to the south, Portland, Oregon, he lost a previous principal positions for being gay, has worked in too many conservative school districts, and was looking for a new place for him, and his partner/fiancé at the time G, to settle down. When he came to Ashland to tour the town before his 6-month interview process for the Superintendent position began, he had the same experiences I did, welcoming people, friendly inhabitants, but he also asked probing questions about life and acceptance in Southern Oregon and Ashland. By the time it came to the interview process, he felt like being gay was actually an asset, he talked about his life and professional experiences and his partner. When he did get the position, it was evident that he was able to be his authentic self here and even be his true self on his personal bio page where he included multiple pictures of him and his partner.

While walking downtown the next day after Pride, we ran into Joseph on his way to one of the candies and sweets stores in town. When we were outside after his purchase, we were interrupted by a woman, she apologized, but she said she had to personally thank him for coming to town. She didn’t have any kids in the school system, but she recognized the great impact Joseph had on the schools and town. As soon as she walked away, I asked him, “Did you pay her to say that?” It was comical, he blushed, but he smiled and reiterated that this is the treament he has had from day one, even before he moved to Ashland, even before he signed on to be the Superintendent, even before the interviews. “This is Ashland, that’s what it’s like living here.”

Clearly, You’re Invited

Somewhere between sipping Pinot in the vineyards, dancing at the Pride after-party, savoring breakfast on my creekside deck, and wandering through a downtown that made you feel like you were home, smiling with and chatting up a storm with complete strangers, I understood why people fall in love with this place. Southern Oregon feels like an invitation—to slow down, to breathe deeper, to explore wider, and to be authentically yourself.