In Southern Oregon, the weather is balmy, the landscape lush, and the cities alive with activity. Local foods abound, the wine culture is booming, and art and theatre are around every corner. Ashland, home to the world-famous Oregon Shakespeare Festival, is the cultural epicenter of this region. A beautiful small college town with great dining, lodging and outdoor opportunities, Ashland makes a great multi-day getaway. Here are some of our favorite destinations and adventures to be found in beautiful Southern Oregon.


Over 80 years ago, a teacher named Angus L. Bowmer proposed a festival of Elizabethan-era plays penned by William Shakespeare. Today, the highly acclaimed Oregon Shakespeare Festival runs February through October, with a dozen plays running in three theatres up to seven days a week. While the festival was founded as a Shakespeare-only troupe, today OSF presents plays of all eras and genres. This season features Shakespeare’s Macbeth, as well as Hairspray and Alice in Wonderland. Summer is the most popular season, and savvy visitors buy their play tickets months in advance. Still, it’s often possible to pick up tickets at the box office the day of a performance; rush tickets are sold at a discount an hour before curtain times. Off-season tickets are even easier to come by.

Requiring no tickets is the Green Show, entertainment presented six nights a week at 6:45 p.m. on the bricks, a public courtyard adjacent to the box office. These fun, short shows range in style from acapella singing to taiko drumming and are free to the public. Another OSF don’t-miss experience is a backstage tour, led by a company member nearly every morning of the week. These walking tours are a great way to learn more about festival history, the amazing effort that goes into productions, and get a glimpse behind the curtain, from the dressing rooms to the set. These aren’t free, but at $20 each are well worth the price.

The theatre culture extends beyond Oregon Shakespeare Festival in Southern Oregon. Check out the Craterian, Oregon Caberet or the Camelot Theaters for more live performance options.

Make a side-trip to Jacksonville, which began as a gold rush town in the 1850s and is home to the Britt Festival a summer-long lineup of concerts in a very pretty and unique outdoor venue in the hills just to the west of downtown. Jacksonville is also a fun destination for shopping, history and wine.


Packed into the downtown blocks surrounding the Oregon Shakespeare Festival are dozens of delightful dining destinations. Standbys like Greenleaf which has been serving excellent sandwiches and salads since the 1980s, are joined by celebrated new arrivals like Mäs, which offers a changing menu based on as many locally grown ingredients as possible. The owners of Mäs gather foods from the forest, the farms and the markets, drawing inspiration from the landscape and local purveyors to shape each day’s meals.

Hither , is another newcomer, serving a small menu of breakfast and lunch that also changes with the flavors of the season. Look for dishes from hash to Coho salmon to a fried egg biscuit sandwich at this spot on Main Street. And don’t forget the coffee—this is Oregon, and we love our cup of joe, even when the weather is warm and the sun is shining. Hither is known for its rotating resident coffee roaster, specializing in a high-quality, low-production roast.

More great coffee can be found within walking distance of downtown. In 2006, Mix Bakeshop came to town, serving Stumptown coffee and a delightful array of baked treats from croissants to cookies. Case Coffee Roasters casecoffee is newer, with two locations—one near Southern Oregon University and the other downtown. Coffee is roasted in small batches and served with savory treats that range from indulgent to healthful. Vegan donut, anyone?

The best Bloody Marys in town are found at Brothers , which serves breakfast and lunch only. This cozy place is always packed and is known for large plates of super-homemade quiches, omelettes, triple chocolate pancakes, barbecue brisket and much more.

Larks at Ashland Springs Hotel is as light and lovely as it is a reliable source for delicious meals. Illustrations of flora and fauna line the walls of this well-lit urban diner, which serves fresh fine dining focusing on local products and accompanied by great cocktails and an extensive, Oregon-based wine list.

On balmy days, don’t miss the chance to eat outside along Lithia Creek. Louie’s of Ashland, Greenleaf Restaurant and Sesame Asian Kitchen all set up tables outside during summer months. The atmosphere is festive and fun in the breezeway along the creek, where guests dine al fresco near the colors and wares of the Lithia Artisans Market


Southern Oregon’s wine footprint is growing like mad. The region is gaining up to 10 new wineries a year, and it’s easy to day trip your way to dozens of vineyards and wineries in the region. Wine Trails such as the Bear Creek Winery Trail and the Applegate Valley Wine Trail have sprung up to help guide visitors, and small tasting shops are found within the city blocks of Ashland, Jacksonville and Medford, too.

Four miles south of Ashland is Weisinger Family Vineyards, where winemaker Eric Weisinger believes in a hands-off approach to wines, letting the land and the grapes speak for themselves. The result is delicious voigniers and sauvignon blancs to be enjoyed in a classy tasting room and outdoor patio. North of Ashland, en route to Jacksonville, is DANCIN Vineyards on the Bear Creek Winery Trail. The 2017 Oregon Winery of the Year sits on lush grounds with a tasting room and piazza. Sip on a zinfandel and nosh on a fresh artisan pizza on the patio under the walnut tree.

Venture into the Applegate Valley and the Applegate Valley Wine Trail for more scenic wine tasting. Red Lily hosts live music on the banks of the river in the summertime, enjoyed with a glass of tempranillo and a small antipasti platter. Longsword Vineyard serves amazing sparkling chardonnays and syrahs, as well as offers hang gliding and paragliding off of nearby Woodrat Mountain for the brave and adventuresome. Schmidt Family Vineyards is down the road and worth a visit just to see its campus. Wander the grounds, visit the rose garden, venture into the greenhouse, and check out the huge lawn, on which you might wish to host your next event.


Step out of town, and nature surrounds you. Southern Oregon is lush and rich with natural grandeur. Two hours north of Ashland, Crater Lake National Park is Oregon’s only national park, and a must-visit if you’ve never seen it. The cerulean blue bowl of water—the deepest lake in North America—will amaze with its beauty and leave lasting memories. The road from the south doesn’t open until summer season, but a stop is well worth the effort in season.

The Rogue River is a terrific waterway for white water rafting, fishing and hiking—a 40-mile trail follows its wild waters. If just a stroll is more your style, visit the Rogue Gorge, which offers a paved trail to an overlook. For adventure, book a one-day or multi-day white-water rafting trip with a guide.

Back in Ashland, Lithia Park is 93 acres natural wonder right in the heart of town. The park is situated on Ashland Creek and includes both undeveloped woods and landscaped acreage. Stroll by a Japanese garden, two duck ponds, a formal rose garden, groves of sycamore trees and a children’s playground.


Ashland Springs Hotel is Ashland’s crown jewel. Listed on the National Register of Historic Places, this lovely, luxurious landmark first opened in 1925 and underwent a restoration and reopening in 2000. Rooms are modest in size but beautiful and comfortable; the lobby is a little natural history museum, with bird taxidermy, eggs and seashells on display; views from upper stories take in the landscape of the valley.

The Peerless is off the beaten track—or on the other side of the tracks, depending on how you look at it. The historic hotel was built in 1904 and offers six rooms and a renowned restaurant. Vintage décor, an award-winning menu and an oversize outdoor patio make this place especially appealing.

Lithia Springs Resort is three miles from downtown Ashland, located on a natural springs that provides waters for the soaking pools and spa onsite. Bungalows, suites and studios are available for overnight guests, and come with a complimentary hot breakfast buffet.

Bard’s Inn is another great lodging option, located within easy walking distance of Ashland theaters. With many rooms including suites, and a swimming pool, this is a great destination for families. Jacksonville Inn built in 1861 during the gold rush, is a good choice for extremely charming lodging and dining in Jacksonville.

Three days in Ashland will go by in a flash, leaving you longing for more of Southern Oregon’s delights. Find more great travel adventures in Southern Oregon at