(Jenny Graham / Oregon Shakespeare Festival)

“All the world’s a stage,” Shakespeare famously penned, and Ashland has hitched its fortunes to that wagon. The

traces its roots to an enthusiastic teacher named Angus Bowmer, who organized its first production in July 1935. Hundreds of plays later, the Shakespeare festival has established itself as one of the nation’s leading nonprofit theaters.

The pandemic and summer wildfires caused the festival to close for stretches, forcing budget cuts, layoffs and fewer performances. Businesses suffered and shuttered. But the 2026 season, which runs into October, includes 10 productions, mirroring prepandemic levels.

Its outdoor Allen Elizabethan Theatre (marked on this map), with seating for nearly 1,200, rotates Jane Austen’s “Emma” with Shakespeare’s “The Taming of the Shrew” and “Henry IV, Part One.”

We took in a couple of productions in the cozy theater space named after Bowmer. The first involved the romantic turns and twists of “A Midsummer Night’s Dream,” proving the Bard’s adage that “the course of true love never did run smooth.” On our last night, the musical “Come From Away” spun a tale of tears, comedy and triumph arising from the 7,000 airline passengers suddenly diverted to Newfoundland on 9/11.

Tip: The

has memorabilia galore, from a Hamlet pen topped with (alas, poor) Yorick’s skull to a tea towel emblazoned with the Bard’s words. They capture my view of the entire shop: “I like this place and willingly could waste my time in it.”

(Alex Pulaski)

Like a fine wine, Ashland’s

just keeps getting better with age. The main building of the family-owned boutique property dates to 1886. It has been lovingly restored inside and out, including a beautiful garden and period furniture in the 23 rooms and suites. Every morning begins with a complimentary two-course breakfast, opening with sliced fruit and pastry. Second-course breakfast options range from omelets to pancakes to steel-cut oatmeal ringed by fresh-cut fruit and granola.

Winchester Inn excels in the details: fresh flowers and afternoon pastry treats in the rooms, 600-thread-count sateen sheets, ultra-comfortable pillow-top mattresses, plush robes. (Note: some rooms involve maneuvering a winding staircase; inquire before booking.) This was our second visit in recent years; it’s proved to be a memorable, romantic, relaxing base for a long weekend stay.

(Alex Pulaski)

Southern Oregon’s scenic Rogue River is a white-water rafter’s paradise — so much so that it was used for filming some scenes for the 1994 movie “The River Wild.” Starting last summer, however, the

on the Klamath River opened a new stretch of rafting to area outfitters.

We took on Kikacéki (Ward’s) Canyon with

, sandwiching the intense, three-mile stretch of Class III and Class IV rapids between two longer, leisurely stretches packed with wildlife and blooming wildflowers. The river stretch, entirely within California’s northern border, showed us bald eagles, osprey, deer, red-winged blackbirds, a peregrine falcon, herons and more. Guide Ian Gannon pointed out the rapid changes in recent months as reservoir muck receded and greenery crowded the river’s reconstituted contours.

It’s a powerful ecological lesson, temporarily forgotten during the adrenaline rush of the challenging canyon itself. This scenic stretch was bone-dry for over a century while water was diverted through a tunnel system. Today, it’s a face-drenching, wave-bouncing, hard-paddling, rock-evading thrill ride serenaded by Gannon’s urging us to “dig in, dig in, dig in.” We did, laughing and hooting loud enough afterward to pry the great blue herons from their rookery, surprised into flight.

(Alex Pulaski)

At

a tiny restaurant that has built a big reputation for its Japanese-influenced menu since opening in a permanent location in 2018, chef Josh Dorcak holds court at a handful of tables and a chef counter. Total seating is for 16.

While sous-chef Devyn Delisle quietly plated intricate dishes, Dorcak maintained a steady soliloquy around the thoughts and sourcing behind the selections, as well as the accompanying wines and sakes. Much of this work, Dorcak said, is about creating connections.

“This is my orchestra,” he said. “It’s my songbook. And it’s my house — I’ve spent most of my 30s here. It should be a personal experience — I’m cooking your food.”

And so on, through nine sublime tasting courses, from lobster to abalone to bluefin tuna to lamb. More than a meal, it is a sensory experience.

(Alex Pulaski)

A carpet of purple vetch welcomed us on the drive up to Grizzly Peak, which at 5,922 feet commands views of surrounding mountain ranges, Ashland and nearby Medford. The

revealed wildflowers along much of the nearly five-mile loop, from white trillium in abundance to bright clumps of Indian paintbrush.

The well-marked trail can be hiked solo, but for newcomers or anyone wanting to learn more about the flora and geology, owner/guide Nathan Dwyer of

offers insights into the medicinal properties of plants such as yarrow and elderberries. Or he will explain the difference between a corn lily and a fawn lily.

After the hike wandered past maples and firs bearded with lichen, Dwyer let us know that even more was in store. “The fireworks are about to go off,” he said. His meaning became clear when we spotted snow-topped Mount Shasta and other landmarks, including

Emigrant Lake stretched out below, and ant-sized vehicles climbed toward the Siskiyou Pass, the highest point on Interstate 5.

Dancin Vineyards near Jacksonville.

(Alex Pulaski)

The warm-weather counties of Josephine and Jackson comprise southern Oregon’s

home to about 45 wineries. Eric Weisinger’s family pioneered winemaking in the area when they opened in 1988. But unlike the Willamette Valley near Portland, which has tied its reputation primarily to Pinot Noir, he says, “the biggest challenge for this area is it’s still trying to find its identity.”

(marked on this map) is now focusing more on Tempranillo, as well as rosé, Sauvignon Blanc, Gewürztraminer and more. Weisinger himself can often be found in the tasting room, with its expansive deck. He also lends his winemaking skills to others, such as the newly opened

midway between Ashland and Jacksonville.

Owners Brian Sephton and Anita Klingenberg started planting vines on 25 acres in 2021, and are just bottling their first Pinot Noir. In the meantime, they have debuted a Dark Hollow Chardonnay, a Riesling, a distinctive blend of Sémillon and Sauvignon Blanc, and more. Bucking convention, they also planted Spanish and Italian olive varieties, and are pressing their own olive oil. You can taste the Spanish blend (the Italian is sold out) alongside their wines on the tasting room’s shaded deck. It’s a small family operation, and visitors can expect personal attention.

For a picture-perfect setting that combines vineyard views, well-crafted wines and a memorable menu of stuffed mushrooms, other small plates and pizza, try

just outside of Jacksonville. The Marca family makes award-winning Chardonnay, Pinot Noir, Barbera and more.

(Alex Pulaski)

You wouldn’t be wrong thinking that the red brick storefronts of

, about a half-hour drive from Ashland, look like something from an 1800s Old West movie set. Hollywood filmed there for 1972’s “The Great Northfield, Minnesota Raid,” with Robert Duvall playing the part of legendary badman Jesse James.

Once a thriving gold boomtown, the city is now designated as a U.S. National Historic Landmark. Buildings that in the 1850s and 1860s were blacksmith shops, tin shops and saloons live on as toy stores, boutiques and, well, saloons. Eileen Bobek opened the beautifully curated

(marked on this map) in a tiny space in 2017. The shelves are packed, but there’s room for a stuffed chair and a love seat. And there’s time for conversation.

“I like to say that we’re successful in every way other than monetarily,” Bobek said. “We’re creating a space you can love, fulfilling a community need and putting books in front of people that they might not have seen before.”

Every summer, Jacksonville’s

showcases a series of outdoor concerts. This summer’s lineup ranges from David Lee Roth to orchestra to Portugal. The Man.

(Alex Pulaski)

Between the indoor and outdoor pursuits, it’s worth taking an hour to soak tired muscles at

in Ashland. Founded by a chiropractor, the soothing Japanese baths are complemented by a variety of optional massage and other spa treatments. There’s also a tea and sake lounge with light snacks and sweets.

We kept it simple, just soaking in a private pool (set at 104 degrees) in a small courtyard where jasmine and honeysuckle vines climbed the walls and basil and other greenery filled planters. Then a quick dip in a cooler plunge pool and a visit to the dry sauna. Pure relaxation.

(Alex Pulaski)

Ashland is a living green space — the

spread over more than 800 acres. At nearly 100 acres, centrally located

is the city’s jewel, following Ashland Creek. Walking trails under a canopy of shade trees pass by duck ponds, a children’s playground and picnic benches. There are also courts for tennis, pickleball and volleyball, a rose garden, and a Japanese garden.

Another green space,

, includes a trail system that leads to gurgling Bear Creek. It’s a peaceful spot where bird calls abound. In addition to recreational fields, the park includes an interpretive center (open 9 a.m. to 1 p.m. on Tuesdays and Thursdays) and a lovely volunteer-tended pollinator garden. While exploring the park, keep your eyes open for wild turkeys and deer.

(Alex Pulaski)

A magical feel for the young and young at heart pervades TreeHouse Books, with its whimsical mix of cards, games and journals, and a wonderful breadth of reading for kids and teens. It’s been around nearly half a century — the last 16 years under the current owners.

You can’t miss the “Secret World” vault of young adult books in the back, but look closely on the way in or out of the store’s front door. There along the steps sits a tiny gnome door for otherworldly visitors. The shop hosts enchanting family-friendly events like a “gnomecoming party” with a lantern procession, a stroll through Lithia Park for “the waking of the pollinators,” and a recent midsummer tea party with a hunt for secret fairy houses.