Surrounded by the rolling hills of Southern Oregon, the town of Ashland combines small-town warmth with world-class culture. Whether you arrive by a short flight into nearby Medford or enjoy a scenic drive through the Rogue Valley, every season offers something special, but from March through October, the town truly comes alive with the energy of the Oregon Shakespeare Festival.
Begin your morning at MIX Bakeshop in the heart of Ashland Plaza, a friendly local spot with the charm of a Paris sidewalk café. Grab handcrafted coffees and fresh morning pastries to enjoy on a leisurely stroll through Lithia Park, Ashland’s crown jewel.
Established in 1908, Lithia Park’s 93 acres are a haven of natural beauty and hold the distinction of being the oldest park in the region. Wander through its lush gardens, creekside trails, past duck ponds, and a Japanese Garden. Pause for a moment on a bench; you may just be treated to the sounds of musicians performing live within the park during the Oregon Shakespeare Festival season.
Head back to Main Street for lunch at Greenleaf. The quaint eatery is known for fresh flavors and views from its outdoor patio situated out back along Ashland Creek. The sweet little alleyway is lined with cozy restaurants and umbrellaed seating and hosts the Lithia Artisans Market on weekends mid-March through October.
As the afternoon stretches ahead, take time to explore Ashland’s many boutiques and art galleries. Each one offers unique treasures such as handcrafted jewelry, fine art, or locally made goods.
If you have time, be sure to stop by the historic Ashland Springs Hotel. The grand landmark celebrated its 100th year and stands as a proud symbol of the town’s elegant past.
By late afternoon, you’ll be ready to check into Lithia Springs Resort and Wine Garden for the duration of your stay and a refreshing pause before dinner. With its tranquil gardens and grounds, mineral spring waters, and an inviting mix of bungalows, suites, and studio accommodations—along with a day spa, saltwater pool, and tasting room—it’s the perfect place to unwind.
After a rest, it’s time for dinner at downtown Ashland’s Bar Juillet for laid-back sophistication at its finest. The chic wine and cocktail bar offers a menu of seasonal small plates and comfort classics. Don’t miss the standout fried chicken—crisp, golden perfection drizzled with Ted’s honey, and paired with Aleppo chili and Calabrian ranch.
Of course, no visit to Ashland is complete without an evening at the Oregon Shakespeare Festival (OSF). OSF has transformed this small town into one of the nation’s most vibrant theatre-going destinations since 1935. Tickets for the next season are released each year in late November, but you’ll soon realize that Ashland’s magic lingers long after the curtain falls.
Plan your trip at Travel Ashland Oregon.
By Emily Molina