This Is One of the West Coast’s Most Charming Small Towns—With Festivals, Mountain Views, and Easy Wine Country Access

Key Points

• Ashland, Oregon, is a charming mountain town known for its historic Oregon Shakespeare Festival, Victorian architecture, and thriving arts scene.

• Visitors can enjoy scenic hiking trails, mountain biking, whitewater rafting, skiing, and wine tasting in the surrounding Rogue Valley.

• The town offers acclaimed farm-to-table restaurants, boutique hotels, historic inns, and mineral-rich hot springs for relaxing getaways.

It's been hundreds of years since his death, and yet, Shakespeare remains one of the most influential figures in literature and the performing arts. For fans of the Bard, planning a trip to his stomping grounds in Stratford-upon-Avon or attending a play at the Globe are essential pilgrimages. But there's another place Shakespeare devotees should have on their itinerary, and that's Ashland, Oregon, home of the Oregon Shakespeare Festival .

Founded in 1935, the Oregon Shakespeare Festival puts on a suite of plays and performances across its three theaters (one of which is among the oldest Elizabethan-style theaters in the country). It's helped put Ashland on the map as a center for arts and creativity, but it's just one of the reasons this Southern Oregon town is worth a visit.

Located just half an hour from the border with California, Ashland is a mountain-hugged community nestled among the Cascade and Siskiyou ranges. Within city boundaries, it's the quintessential picture of small-town charm: elegant Victorian homes, quaint shopping streets, leafy parks with babbling brooks. Minutes away among the mountains, it's a different world, with wooded hiking paths, ski hills, whitewater rafting, and lovely landscape views for miles. Thanks to the agricultural abundance of the surrounding Rogue Valley—a fruit-famous region that is home to the renowned Harry & David pear company—there are wineries to enjoy, farm-to-table feasting, regional food festivals, and a culinary trail. The region's wine scene in particular is attracting more and more attention, luring oenophiles south from the Willamette to discover what winemakers in Southern Oregon have been cooking up—the Shakespeare Festival is truly just the tip of the iceberg.

Here's what you need to know before planning a trip to Ashland, Oregon.

Best Things to Do

Ashland is all about art. During your visit, your first priority should be to catch a play during the Oregon Shakespeare Festival , which runs seasonally from March through October. If it's performing arts you're after, there's also the Oregon Cabaret Theatre and the Rogue Theater Company , plus gatherings like the Ashland New Plays Festival where theatergoers get to see fresh new works. If your tastes tend more toward the visual arts, plan visits to the Schneider Museum of Art , the Ashland Art Works collective, and the many galleries and artist studios around town. There's also the First Friday Art Walk, a monthly ritual involving popping into galleries to meet artists, catch live music shows, and watch demonstrations.

Ashland also has a calendar packed with events which occur throughout the year such as the Ashland Independent Film Festival , the Festival of Light Celebration for the holidays, and the snark-filled Ashland Sarcasm Festival , to name a few.

Hopping around to theaters and galleries gives you a chance to explore the city proper. With its quaint buildings, restaurants, galleries, and shops, the downtown core is an utterly charming place to pass a few (or many) hours. Ashland is also a featured stop on the Oregon Film Trail, having served as a filming location for the 2014 movie Wild (which starred Reese Witherspoon), and inspired the town of the 2009 stop-action animated flick Coraline , so some areas, like the Ashland Plaza and the town's many Victorian and Italianate homes, may already seem familiar. Be sure to pop into Lithia Park next door, which has walking paths, a Japanese garden, and historic landmarks.

With wild rivers, thick forests, and two mountain ranges at its doorstep, Ashland also has plenty to offer in the outdoor adventure department. Thanks to the exhilarating trails of the Ashland Watershed, the city is a world-renowned mountain biking destination. Grizzly Peak is a popular hiking spot due to the sweeping views from its nearly 6,000-foot summit, and some routes, like the Bandersnatch Trail, are accessible right from town. You can also take a day hike along the Pacific Crest Trail. Nearby lakes and reservoirs like Emigrant Lake and Howard Prairie Lake offer fishing, boating, and camping, and intrepid adventurers can head to the Rogue and Upper Klamath Rivers for a day of whitewater rafting. If you're willing to drive a bit further in search of natural wonders, you'll be well rewarded; Crater Lake National Park , the deepest lake in the country, is a two-hour drive north, or head west to explore below the surface of the earth in the Oregon Caves National Monument & Preserve . Come winter, there's also skiing at the Mt. Ashland Ski Area .

Where to Eat and Drink

One essential thing travelers should bring to Ashland? Their appetites. Fueled by creative energy and supplied with fresh fruit, vegetables, and other local goodies from the farms of the Rogue River Valley, Ashland is one of southern Oregon's best places to wine and dine.

True to form for a town that loves theater, dining out here is extremely atmospheric and full of artistic flair. There's Hearsay , which serves New American cuisine in a mural-covered dining room housed within a former church. Inside a historic Victorian-style home-turned-inn, Alchemy Restaurant and Bar transforms raw ingredients like wild mushrooms into fanciful dishes. At Lovejoy's Tea Room, the elegance and ritual of a British high tea comes to Oregon's rugged southern mountains. One must-snag reservation while in town is Mäs ; run by chef Jack Dorcak, this intimate tasting menu spot for "Cascadian" cuisine has caught the eye of The New York Times and the James Beard Awards in recent years, bringing national buzz to the local food scene. If a reservation eludes you, head instead to Dorcak's other culinary ventures: Nama for izakaya (Japanese gastropub) and seafood fare followed by cocktails at Kando .

Downtown is where you'll find the bulk of the town's restaurant scene, from Italian at Osteria La Briccola to New American at Cocorico . But you'll want to branch out beyond downtown as well to grab breakfast at The Breadboard Restaurant , a beloved local diner, or indulge in a beer and burger at Caldera , a brewery and restaurant. Branching out is also essential for dipping your toes into the local wine scene. Ashland sits within the Rogue Valley American Viticultural Area, a wine region on the rise—it's also considered the birthplace of Oregon winemaking, as the state's first official winery launched here in 1873. Stop into nearby establishments like Grizzly Peak Winery , Irvine & Roberts Vineyard , and Belle Fiore Estate Winery for tasting flights in scenic tasting rooms. Many more wineries can be found around Medford, Oregon, and in the Applegate Valley area, so I recommend booking an outing with a tour operator such as Wine Hopper Tours to fully indulge without worrying about driving.

While it's a bit of a drive, no trip to the area is complete without popping up to Central Point to visit Rogue Creamery . This cheesemaker has gained global fame for its award-winning blue cheese, which in 2019 was declared world champion at the World Cheese Awards; the first American cheese to win the distinction—and first American cheese to win the distinction. The broader Rogue Valley around Ashland also has a food trail worth following, which connects farms, restaurants, breweries, and wineries.

Where to Stay

Set just steps from the Oregon Shakespeare Festival and downtown, the Ashland Springs Hotel is perfect for being at the heart of Ashland's artsy action. Over a century old, she's a grand dame of a property, with 70 sunny, cozy rooms and a standout restaurant. Many of the town's historic Victorian homes have also been converted into elegant inns and bed-and-breakfasts, like The Winchester . This blue-accented beauty has gourmet breakfast, charming rooms, and lauded dining at the on-site Alchemy.

Historically, Ashland was also sometimes referred to as the Baden-Baden (a historic German spa town) of America thanks to its healing mineral waters, drawing visitors from near and far seeking restorative baths. That tradition continues at Lithia Springs Resort & Wine Garden , a wellness retreat just outside of town. Nearly all the rooms and suites feature deep soaking tubs for full immersion in the sulfur-rich waters, with heated outdoor pools and hot tubs as well. Serene gardens provide relaxing places to unwind in nature, best accompanied by a glass of Southern Oregon wine in the wine garden area.

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