Photo: T. Charles Erickson, courtesy of Oregon Shakespeare Festival
Arts & Culture in Ashland
Come to Southern Oregon for the theater, mountain views, and wine country road trips
Nestled in the Siskiyou Mountains of Southern Oregon and known for its lively theater scene, Ashland offers some of Oregon’s best cultural and outdoor experiences. Solo travelers in need of artistic inspiration enjoy meandering from show to gallery to boutique, while nature lovers take advantage of a large park in the middle of town and hikes into the surrounding hills. Downtown, visitors find excellent dining, and a quick drive offers wine tasting in the award-winning Rogue Valley.
Photo: Jenny Graham/courtesy of Oregon Shakespeare Festival
Discover
Anchored by the Oregon Shakespeare Festival (OSF), which celebrated its 90th anniversary in 2025, Ashland’s art and culture scene is hopping. The festival takes place downtown in several venues from March through October, and plays range from the latest production by contemporary playwrights to a new spin on Shakespeare’s works. Free evening performances take place at the Green Show stage, an outdoor venue offering shows five nights a week from June through September.


Left Photo Courtesy: Oregon Cabaret Theatre | Right Photo Courtesy: Ashland Fringe Festival
The OSF isn’t the only entertainment in town. Watch seasonal comedies and musicals in a converted church at the Oregon Cabaret Theatre, or spend a weekend at the Ashland Fringe Festival, with offbeat and experimental plays each May. At the OSF gift shop, browse the wall of screenplays for recent seasons; or for a deeper dive into literature, check out independent bookseller Bloomsbury Books with specialty mystery titles from local authors. Be sure to wander downtown through local boutiques and galleries including woman-owned ART on FIRST, a collective of more than 40 artists from Ashland and beyond.
Photo Courtesy: gettyimages.com/Saturated
Play
The heart of Ashland, 93-acre Lithia Park draws a wide range of visitors, and offers attractions that span from a pond filled with social ducks to a formal Japanese garden. Find your way along tree-lined paths to Butler Bandshell for free summer concerts, or just to soak in the verdant foliage, flowers and peaceful nature.

Photo Courtesy: Travel Medford
For a longer adventure in the area—particularly nice in May and June during the peak of wildflower season when blooms line the paths—traverse the 2.2-mile Green Springs Mountain Loop Trail about 20 miles southeast of town, or mosey around Mount Ashland’s summit, about 24 miles southwest. Northeast of Ashland lies Crater Lake National Park—a bucket-list destination for many visitors—and the route on the Rogue-Umpqua Scenic Byway provides cool waterfalls, rushing rivers and charming mountain towns along the way.
Photo Courtesy: Herrett Center for Arts and Science
Indulge
Ashland’s excellent culinary scene tempts a sophisticated theater-going crowd. For French-style pastries and Stumptown coffee specialties, head to Mix Bakeshop on Ashland Plaza before a stroll in Lithia Park or shopping downtown. For a heartier breakfast, sit down for omelets or lemon-ricotta stuffed French toast at Morning Glory, a cafe that greets diners with colorful murals decorating a bright blue and yellow interior.
Casual lunch offerings abound, and the local favorite Greenleaf tempts with seating along a burbling creek, where visitors can enjoy the restaurant’s diverse menu. Try a healthy grilled tofu and veggie wrap, salmon chowder or a traditional Reuben sandwich.


Left Photo Courtesy: Bar Juliet | Right Photo: Marsela Mendoza, Courtesy, Greenleaf
For dinner and drinks before a show, diners can’t go wrong with a traditional Indonesian feast at Blue Toba, where Sumatra-born chef Birong Hutabarat serves dishes such as beef rendang curry and coconutty grilled chicken, accompanied by drinks infused with Indonesian flavors. A relative newcomer to town, Bar Juillet has fresh, creative vegetable-driven small plates and house-made pasta with plenty of Oregon wines to pair. For sashimi and whimsical creations like Japanese-style hotdogs, try NAMA, an izakaya that bills itself as “elevated surf and turf,” headed up by James Beard Award semifinalist chef Josh Dorcak.


Left Photo Courtesy: Good Juice Wine | Right Photo Courtesy: Nama
Wine lovers will want to sample a tasting flight of natural wines at Good Juice Wine Shop in town, or take a day or more to indulge in exploring the historic Rogue and Applegate valley’s viticultural areas. With a warmer climate than Oregon’s northern wine regions, this AVA has an exciting mix of warm-weather varietals influenced by Spanish and Italian winemaking traditions, cheerfully served at family-owned tasting rooms.
Photo Courtesy: Lithia Springs Resort
Stay
To experience the Ashland of yesteryear, arrange a stay in one of the unique rooms at the century-old Ashland Springs Hotel, a gleaming white building in the center of town. The top floors of the nine-story landmark offer spectacular views of the surrounding mountains, and the public is welcome at its luxurious spa and farm-to-table restaurant, Larks. Even if travelers are unable to stay, a visit to the grand lobby—with its cozy fireplace, restored woodwork and wraparound mezzanine—is a must.

Photo Courtesy: Ashland Springs Hotel
For a quiet stay within walking distance of the theaters, check out boutique Ashland Creek Inn, which has 10 creekside suites with private entrances and decks. Northwest of downtown is the 38-room Lithia Springs Resort, which sits atop lithium-enriched hot springs deep underground. Here, slightly sulphurous thermal water is piped directly into your room’s soaking tub. Don’t miss the Wine Garden tasting room, where the host offers glasses and flights for an excellent introduction to Rogue Valley’s local wineries and even more relaxation at the on-site spa.


Left Photo Courtesy: Larks | Right Photo Courtesy: Ashland Creek Inn
Kid- and pet-friendly Ashland Hills Hotel & Suites is a popular affordable option on the eastern outskirts of town. This updated motorlodge has 200 suites on a property spanning 14 acres, with an outdoor pool and pickleball court. Thoughtful touches from colorful retro-modern decor to complimentary loaner bikes add to the fun.
Plan A Trip: For inspiration, information and deals for your next trip, download the AAA Mobile app and find maps plus discounts on restaurants, lodgings, and more. AAA.com/mobile.




















