What to Do in Ashland: Attractions Beyond the Wine
Ashland, Oregon may be known for its vineyards and rich winemaking culture, but there’s far more to this charming town than swirling glasses of Pinot Noir. Tucked into the foothills of the Siskiyou Mountains, Ashland is a rare blend of small-town charm, vibrant creativity, and natural splendor. Whether you’re visiting for a weekend or staying awhile, Ashland offers plenty to explore beyond the tasting room.
From award-winning theater and farm-to-table cuisine to scenic hikes, music, and art, here’s a guide to everything you can do in Ashland—wine optional.
Discover the Oregon Shakespeare Festival
One of Ashland’s crown jewels is the world-renowned Oregon Shakespeare Festival (OSF), a must for anyone interested in theater. Running from late spring through the fall, OSF features a rotating schedule of classic Shakespeare plays, modern dramas, musicals, and contemporary works—all performed with exceptional talent and creativity.
Three distinct theaters (indoor and outdoor) host the festival’s varied productions, including the iconic open-air Allen Elizabethan Theatre, which offers a magical setting for summer evenings under the stars. Even if you’re not a diehard Shakespeare fan, the artistry, energy, and innovation of OSF productions are undeniably compelling.
If you’re planning to attend, book your tickets in advance—they sell out quickly, especially during peak season.
Explore Lithia Park
Just steps from downtown, Lithia Park offers a 100-acre sanctuary of trails, gardens, and meandering paths along Ashland Creek. Designed in part by John McLaren, the landscape architect behind San Francisco’s Golden Gate Park, Lithia Park is an idyllic place for a morning walk, an afternoon picnic, or some quiet time among the trees.
Highlights include:
- Japanese-style gardens and duck ponds
- Shady hiking trails that lead into the surrounding hills
- Playgrounds and open lawns for families and casual relaxing
- Concerts in the park during summer months
In every season, the park reflects the shifting beauty of Southern Oregon’s climate—lush and green in spring, sun-dappled and vibrant in summer, and rich with golden leaves in the fall.
Stroll Through the Ashland Plaza and Downtown Shops
The heart of Ashland beats strongest in its downtown Plaza, where historic buildings house a collection of local shops, galleries, bookstores, and boutiques. It’s a walkable, lively hub filled with independent spirit and friendly conversation.
Stop by a local artisan store for handmade jewelry or ceramics, pop into Bloomsbury Books for a cozy browse, or visit a local art gallery to discover the creative pulse of the region. Ashland’s downtown is also home to a variety of cafés, bakeries, and chocolate shops where you can enjoy a sweet break.
For those with a taste for live performance, small music venues and pop-up performances often dot the downtown area, giving a delightful soundtrack to your afternoon exploring.
Indulge in Ashland’s Culinary Scene
Ashland’s culinary offerings are as diverse and elevated as its cultural scene. From fine dining restaurants to quirky local favorites, the town is full of flavor and surprises.
The emphasis here is on fresh, seasonal, and locally sourced ingredients, often with a strong farm-to-table ethos. Many chefs in Ashland work directly with local farmers and foragers to create menus that shift with the seasons.
You’ll find:
- Creative vegetarian and vegan fare
- Fresh seafood and river trout
- Innovative fusion cuisine
- Artisan baked goods and desserts
For a more refined evening out, you might consider a fine dining experience in the hills just outside town. One such spot, Belle Fiore, offers an intimate culinary experience often paired with their estate wines—though the focus here is truly on the food. It’s also a local favorite for seasonal live music events, where guests can enjoy jazz, acoustic, and folk performances with sweeping views of the valley. These relaxed, open-air evenings are a beautiful way to experience Ashland’s food and music culture in one place.
Take in the Art Scene
Ashland punches well above its weight when it comes to the arts. The town is full of galleries, studios, and installations, and every First Friday of the month, you can join the Art Walk, when galleries open their doors late to host new exhibitions, artist talks, and live music.
You’ll find everything from abstract sculpture and mixed-media pieces to classical painting and glasswork, all crafted by regional and nationally known artists. This vibrant art community is a reflection of Ashland’s open-minded, creative spirit—and it’s incredibly accessible, even if you’re just strolling with a coffee in hand.
Get Outside: Hiking, Biking, and Lakes
If you’re drawn to the outdoors, Ashland delivers in a big way. The surrounding landscape offers a wealth of trails, lakes, and mountain vistas just minutes from town.
Try:
- Hiking Grizzly Peak for panoramic views of the valley
- Exploring Emigrant Lake for paddleboarding, kayaking, and picnicking
- Mountain biking in the Ashland Watershed
- Snowshoeing or skiing at Mount Ashland in the winter months
The proximity of town to nature is one of Ashland’s most enchanting qualities. You could spend your morning hiking to a ridge, your afternoon strolling a gallery, and your evening at a world-class play—all without ever feeling rushed.
Soak in the Music Scene
Live music is another layer of Ashland’s cultural fabric. Whether it’s bluegrass in the park, jazz at a candlelit venue, or a classical quartet in a vineyard, music in Ashland is everywhere—and it’s often free or low-cost.
One standout destination is Belle Fiore Winery, where you’ll find seasonal live music nights set in a peaceful vineyard atmosphere. Their music series blends well-known local artists with scenic views and relaxed ambiance—perfect for a sunset glass of wine and an evening under the stars.
Treat Yourself to Wellness & Spa Experiences
If your idea of relaxation leans more toward self-care and restoration, Ashland has you covered. The town is home to several holistic wellness centers, spas, and yoga studios offering everything from massage therapy and acupuncture to sound healing and forest bathing.
Many visitors incorporate these experiences into their trip as a way to reconnect and unwind. After all, Ashland’s pace encourages you to breathe more deeply and take things a little slower.
Make It a Multi-Day Escape
The magic of Ashland isn’t in a single attraction, but in how all of its experiences come together: theater and nature, food and art, music and movement. To fully appreciate everything the town has to offer, give yourself at least a few days to explore.
Stay in a cozy bed and breakfast, a boutique hotel, or one of the many charming vacation rentals. Take your mornings slowly, your afternoons adventurously, and your evenings indulgently. Whether you’re here for a solo getaway, a romantic weekend, or a family trip, Ashland has a way of drawing you in and making you want to stay just a little longer.
More Than Wine
While it’s tempting to plan your trip around wine—and you certainly should include a stop or two for tastings—Ashland offers so much more than a glass of red or white. It’s a place where the arts thrive, the food is honest and inspired, and the beauty of the natural world is always just around the corner.
Whether you’re here for the theater, the trails, the music, or the quiet beauty of a summer night at a vineyard patio like Belle Fiori’s, you’ll find that Ashland leaves a lasting impression, long after the last curtain call or final note of the evening.
It’s more than a destination—it’s an experience.