Meet the Ashland You Haven’t Discovered Yet
By Linda Kissam
Found in Southern Oregon’s Rogue Valley, Ashland is a welcoming destination known for its vibrant arts scene, beautiful natural surroundings, and charming downtown. Famous for the Oregon Shakespeare Festival, the town offers far more than theater, with independent shops, local restaurants, interesting cafés, galleries, wineries, and nearby hiking trails. Whether you’re visiting for a weekend of performances, a relaxing getaway, or a taste of Southern Oregon’s culture and scenery, Ashland makes it easy to slow down and enjoy the experience.
Watch this Big Blend Radio “Sip, Savor & Travel” Podcast episode below with producer Lisa D. Smith, host / travel writer Linda Kissam “Food Wine & Shopping Diva” & Katharine Cato, Director of Travel Ashland. You can also listen to or download the audio version on Podbean.
Katharine Cato, Director of Travel Ashland, joins me to share the often-missed magic of Ashland, Oregon. She takes a deep dive into what Ashland has to offer beyond its famous Shakespeare Festival, “While Ashland is most widely known for the Oregon Shakespeare Festival, which serves as the cornerstone of its culture, Ashland offers year-round amenities and experiences that are attracting a younger demographic from new flight and drive markets, including Portland, Seattle, and Los Angeles.”
Let’s discover what you can expect beyond the Shakespeare Festival experience.
For a relaxed start, all my coffee lovers should begin downtown with a great cup of coffee, then stop for tea or pastries later in the day at Lovejoy’s Tea Room. If you’re particularly interested in specialty coffee, ask whether the café has a signature drink or is serving a current single-origin or pour-over selection. Case Coffee Roasters is an excellent first stop. They were the first to introduce me to putting a whole marshmallow in my latte. Maybe life-changing … just saying. Local offerings and ownership can change, so it’s always wise to verify hours and menus before going.

Sip, savor, and make memories in Ashland, Oregon. Photo courtesy of Travel Ashland.
Wine and culinary experiences are also a major draw. In my opinion, Oregon wines can hold their own among the best wines available to aficionados. The Rogue Valley was recently recognized as the No. 1 Best Wine Region by USA Today’s Readers’ Choice awards. As the southernmost American Viticultural Area in Oregon, Ashland is surrounded by wineries producing approximately 70 varieties of wine. That is a whole lot of wine for visitors to try.
Ashland has more than 100 restaurants, and creative chefs offer distinctive culinary choices. Local produce, regional artisans, and thoughtful menus make dining here memorable. According to Ms. Cato, “From the Chocolate Festival to First Fridays, Ashland’s events showcase the culinary scene.” I say, experience what “taste the place” really means.

Shopping adventures in Asheland. Photo: Steve Heinrichs Photography, courtesy Travel Ashland Oregon
Wellness travel is a trendy big deal, and Ashland fits right into that destination mix. The global wellness tourism market is projected to reach approximately $1.2 trillion by 2027, driven by growing consumer awareness of health and wellness and an increasing interest in repeat wellness travel. Ashland is a beloved destination for girlfriend getaways, with spas, open spaces, and beautiful scenery. I can really get into the whole spa culture.
Unique shopping is a passionate pastime of mine—anywhere, anytime. Ashland seems less about finding a particular chain store and more about discovering the creativity and character of the region. From local artwork and vintage treasures to gourmet foods and literary gifts, the city offers plenty of opportunities to take home something distinctive.

Escape to Ashland for a little wellness, friendship time, and outdoor serenity. Photo: Travel Ashland
Plan to wander, explore the side streets, and enjoy the relaxed pace that makes shopping in Ashland part of the travel experience.
Outdoor lovers will find the experience here to be one of a kind. Believe it or not, Ashland’s trails are not crowded, and you won’t encounter tons of people gathered at the trailheads. With more than 50 miles of easily accessible trails, there are plenty of opportunities to explore responsibly and enjoy the outdoors.

Mountain Biking fun in Ashland. Photo: Aaron Thielsen, courtesy Travel Ashland
Ms. Cato reminds us that, “Mt. Ashland Ski Area offers summer and winter fun, providing runners, hill climbers, mountain bikers, and all others incredible adventures set against the backdrop of a culturally rich downtown and 93-acre Lithia Park, right off the Plaza.” Less competition on the trails? Magic.
If you’re interested in arts and culture, Ms. Cato shares that Ashland offers “365 days of theater, the Ashland Gallery Association’s First Fridays, artist studio tours, live art to see, and the Schneider Museum of Art.” The Playwrights’ Walk is another new series of bronze installations featuring famous quotations.

Enjoy the show! Photo courtesy of Epic Ashland and Travel Ashland
Events throughout the year include hill climbs, mountain bike races, Ashland Mystery Fest, the Ashland Independent Film Festival, the Southern Oregon Pride Festival, the Oregon Chocolate Festival, the Festival of Light, Fourth of July celebrations, and the Children’s Halloween Celebration.
Sounds like a lovely weekend plan to me. Enjoy your time in this very special place.
Plan Your Visit at: TravelAshland.com
Linda Kissam is a professional travel, food, and wine writer based out of Arizona and the Pacific Northwest, who specializes in easy, breezy destination stories sharing her favorite things about the places she visits. Visit FoodWineTravelChix.com
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