A Journey of Discovery, Connection, and Inclusion
Southern Oregon Wine Country is an oenophile’s dream destination waiting to be discovered, offering awe-inspiring vineyard vistas, exceptional wines, and charming accommodations to suit every preference. In the southwest region of the state, the Southern Oregon AVA stretches a remarkable 125 miles from the vibrant city of Eugene to the tranquil California border, and spans 60 miles between the Cascade Mountain Range to the east and the Coast Range to the west. This geographically diverse area encompasses six distinct appellations, with the renowned Rogue Valley and Applegate Valley serving as perfect starting points for my first visit, each offering unique terroirs and wine styles.
However with my excitement, though, came an honest reckoning. Southern Oregon isn’t exactly known for its racial diversity, and the thought of stepping into unfamiliar small towns as an African American traveler carried its own set of concerns. Would I feel welcomed? Would my presence stand out uncomfortably? These questions lingered as I planned my 72 hour journey. However, I chose to project my hope onto the universal appeal of wine—the way it has the power to bring people together, transcending differences and fostering warm human connections over a shared appreciation. Thankfully, that hope wasn’t misplaced. From culinary delights in the downtown areas of Ashland and Medford to conversations with winemakers in the Rogue Valley, I was met with kindness and enthusiasm, making the experience not only enjoyable but heartening.
Here’s a comprehensive itinerary to make the most of your time and prepare you for further discoveries in the captivating wine country of Southern Oregon.
First 12 Hours: Arrive, disembark, and enjoy a glass of wine, all within 15 minutes
MORNING
For those eager to get wings up and wine down promptly, start your wine adventure in Medford, Oregon. After a swift 75-minute flight from San Francisco Airport to Rogue Valley International-Medford Airport, head to Dancin Vineyards. Just a 15-minute drive, or 7.7 miles from the airport, this winery is celebrated for its award-winning Pinot Noir and Chardonnay, which reflect the region’s distinctive terroir.
Relax on the expansive patio with a glass of their silky Pinot Noir, savoring its complex dark cherry and spice notes, while enjoying artisanal wood-fired pizza or a leisurely Sunday brunch. While waiting for the Margherita pizza, I fed the koi fish in the nearby pond. Their vibrant orange and yellow hues brighten any season or mood. With a glass of 2023 En L’air Rosé of Pinot Noir in hand, I tossed fish food with the other, feeling a sense of tranquility and connection to nature.
AFTERNOON
Next, visit Weisinger Family Winery, close to the artistic town of Ashland. This boutique winery specializes in small-batch, handcrafted wines that embody the unique terroir of Southern Oregon. Sample their signature Tempranillo or Sauvignon Blanc, both known for their distinct characteristics, while enjoying serene vineyard views that stretch to the horizon. It’s always an honor when the winemaker greets you, but it was especially meaningful as Owner and Winemaker Eric Weisinger introduced himself during the busiest time of the year—HARVEST! Smelling of the vineyard, with nearly knee-high boots and fingers tinged purple, he asked my favorite wine. I replied promptly, “2021 Estate Tempranillo.” He gladly poured another glass before I headed back to my hotel.
EVENING
After a day of exploration, I settled into the charming Ashland Springs Hotel. This elegant hotel seamlessly blends historic charm with modern comfort, offering a perfect fusion of past and present. The beautifully restored building boasts refined decor and cozy amenities, creating a serene retreat that invites you to unwind and rejuvenate. After some time to refresh and recharge, I was hungry to explore Ashland’s vibrant dining scene, celebrated for its diverse culinary offerings. I indulged in a delightful experience at NAMA, a seafood-focused kitchen that expertly elevates surf and turf with its daily selection of sustainably sourced ocean delights. When the server asked for my order, I simply smiled and said, “seafood and sake.” Within minutes, I was presented with a beautifully arranged platter of fresh seafood and a glass of perfectly chilled sake.
24-48 Hours In: Discovering the Rogue and Applegate Valley Wine Country
MORNING
I’m a strong advocate of the motto “Workout before Wine,” typically at the gym. However, since Lithia Park is featured on almost every “Things to do in Ashland, Oregon” list, I decided to take my calorie-burning activity outdoors. Hiking becomes less enjoyable for me after about 5 miles, so I chose the Bandersnatch Trail—a 3.8-mile loop around Lithia Park offering stunning mountain views. My heart rate raised lock step with each movement towards the peak of the trail. As I gazed over the Rogue Valley, I was reminded of the wineries I still need to explore in the area.
AFTERNOON
After a shower and power bar I was ready to explore Troon Vineyard, located in the heart of Oregon’s scenic Applegate Valley. Troon is a pioneering winery known for its dedication to biodynamic farming practices, ensuring that every bottle reflects their commitment to sustainability and harmony with nature. Their diverse wine selection, ranging from robust reds to crisp whites, offers something for every palate. Don’t miss the chance to sample their distinctive Vermentino or rich Zinfandel. Next on our journey was Rogue Creamery Dairy Farm. This family-owned farm has been crafting artisanal cheese since 1935, with a steadfast commitment to sustainable farming methods, evident in every bite. After touring the farm and learning about their process, I couldn’t resist indulging in the abundant free samples. As an avid fan of Rogue cheeses, I shrugged off my protesting stomach, knowing it was well worth it.
EVENING
Dinner at Blue Toba in Ashland, Oregon was an unforgettable experience. This cozy and intimate restaurant was a highlight of my trip, offering an eclectic menu inspired by the rich and diverse flavors of Indonesian and Thai cuisine. As I walked in, the aromatic spices instantly transported me to Southeast Asia, and the inviting ambiance hinted at the culinary journey ahead. I couldn’t resist trying their signature dish, Rendang—a slow-cooked, flavorful beef curry that was tender and infused with a chorus of spices. It was paired with fragrant jasmine rice and crispy, golden-brown tempeh that added a welcomed crunch to each bite.
Clock wines down toward departure
MORNING
I embarked on a Historic Walking Tour of Ashland, Oregon, guided by an insightful and engaging local expert who vividly brought the town’s stories to life. I discovered Ashland’s captivating history, from its origins as a bustling 19th-century mining town to its evolution into a vibrant cultural hub, renowned today for its world-famous Shakespeare Festival. The tour included visits to historic landmarks such as the picturesque Lithia Park and the “Say Their Names” Memorial at Railroad Park, a powerful tribute honoring victims of racial violence. This memorial serves as a poignant reminder of the ongoing struggles for justice and equality.
AFTERNOON
In the afternoon, I visited Tap and Vine in downtown Medford, owned by San Francisco Bay Area native Adam Benson. The relaxed and welcoming atmosphere, combined with an extensive selection of wines, beers, and cocktails, made it an ideal spot for an afternoon refreshment. I decided to mix things up by ordering an Oregon Mule (Wild Roots Huckleberry Vodka, Caldera Ginger Ale, Lime) along with a Smoked Tri Tip Sandwich.
During lunch, Adam Benson mentioned a new project he wanted to show me. We stepped out of Tap & Vine and headed next door to a barbershop. I jokingly informed him that I don’t just let anyone touch my hair, but I appreciated the offer. He replied, “Wait for it.” We walked through the barbershop to a hidden entrance of The Butterfly Club, a chic, speakeasy-style cocktail bar located in an old bank vault. As I entered, I could easily imagine the lively atmosphere at night when the place was open. The dimly lit surroundings and cozy leather booths enhanced the speakeasy vibe, transporting me back to a bygone era. Even though they were technically closed, I was able to order their signature cocktail, The Butterfly Effect (gin, elderflower liqueur, lavender bitters).
EVENING
After exploring Medford, I returned to Ashland for dinner at Harana Cafe, a Filipino restaurant beloved by locals. The cozy, intimate setting and warm hospitality made it a perfect choice for an evening meal. I decided to try their acclaimed Chicken Curry and Pancit (stir-fried noodles), paired with a refreshing Calamansi juice.
To cap off the evening, I attended the Oregon Shakespeare Festival, a world-renowned theater festival that takes place annually in Ashland. This year’s lineup featured exciting plays such as “Romeo and Juliet” and “Hairspray.” I was fortunate to secure tickets for “Much Ado About Nothing” and was thoroughly impressed by the production’s quality. The talented actors, stunning set design, and the overall atmosphere of the outdoor theater left me thinking, never did I desire to see thee theatre more.
Final Thoughts
Traveling through Southern Oregon as an African American can sometimes feel isolating, but it also presents opportunities to affirm belonging and enjoy the region’s beauty. Positive encounters with locals at wineries, on hiking trails, and in towns like Ashland and Medford highlighted the kindness and openness of many. However, there’s still a need for greater inclusivity and representation in regions like this. African American and BIPOC travelers are encouraged to explore, challenge assumptions, and leave their mark, finding joy in experiences. Simply being present is a meaningful act of representation and a step toward inclusivity.
Written by Noël Burgess in partnership with Travel Southern Oregon.
Follow his journey on Instagram @mrnoelburgess.
