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Trip Planner: Autumn in Ashland, Oregon
Fall for Ashland
As the days shorten, the Rogue Valley’s dramatic hamlet is a little spooky and a lot awesome
written by James Sinks
With its renowned theatrical festival, international culinary scene, public university and smorgasbord of outdoor recreation pursuits, it might not feel fair to call Ashland a ghost town.
Then again, you might not be wrong.
Paranormal reports abound in the hamlet in Southern Oregon’s Rogue Valley, from the ghost of a 1930s actor lurking at the Oregon Shakespeare Festival, to one that stomps the hallways at the Columbia Hotel downtown.
“Based on the stories I’ve heard, the spirits here are more mischievous than murderous,” chuckled 74-year-old Peter Finkle, a local historian who leads art and history walking tours. His most popular, by far, explores Haunted Ashland.
Even if you don’t bump into apparitions, you’ll still be spirited away—and quite busy—in Oregon’s drama capital. Zigzag from dusty mountain trails to U-pick fruit orchards to live performances, and from a magic mushroom café to the magical hidden patio at downtown’s Bloomsbury Books—ideal for espresso-nursing in sweater weather.
Platted at the former site of a Shasta Indian village, the city first thrived as a wagon and railroad stopover, and now relies on tourism and hometown Southern Oregon University.
Maybe there’s something in the lithium-laden (and ghastly to your taste buds) local Lithia water, but the community from its early days developed a gentler brand of politics compared to its Southern Oregon neighbors, including its support for President Lincoln and women’s suffrage. Higher local taxes in the now-nicknamed “People’s Republic of Ashland”— including a 5 percent restaurant sales tax—foster a storybook community with enviable parks.
The people’s republic also loves Halloween, and for years even shut Main Street for a giant costume party. But that revelry went by the wayside in the 1980s after the drunk-and-disorderly element got too disorderly and—from the apt metaphor department—a costumed visitor shot himself in the foot.
These days, the city celebrates with a new-ish mystery writing festival in October and a children’s daytime Halloween parade—usually with more costumed adults than kids, said Katharine Cato, Travel Ashland director.
Also, while the city has long been a tourism magnet because of the 90-year-old Shakespeare Festival, it’s no longer the sole attractor. “It’s not uncommon to hear people say they came for the trails … and then discovered we have Shakespeare.”
Day 1: LITHIA PARK • LOCAL BITES • SHAKESPEARE
One of Oregon’s jewels, technicolor-in-autumn Lithia Park begins downtown and parallels Ashland Creek to ponds, a japanese garden, sports courts and trails with names from Alice in Wonderland. First opened in 1892, it’s a perfect setting to grin like a Cheshire cat and work up a post-travel appetite.
You’ll have enticing options.
For a community of 21,000, Ashland’s culinary scene is a diverse delight. Indonesian lunch at Blue Toba completely fits that bill. Chef Birong Hutabarat used to travel personally to gather exotic spices, but now the family restaurant is too busy so his brother sends them. Try anything with his zesty sambal sauce, concocted from four Asian chilis.
In the artsy downtown district, explore galleries, boutiques, a weekend artisan market and a combined gas station and floral shop. Ashland clearly loves its Shakespeare, and you’ll find more than a handful of references, from the Tudor-styled Bard’s Inn to the “As You Like It” sex toy shop.
Towering overhead is the Ashland Springs Hotel, where hopefully you’ll be checking in. Celebrating its centennial this year—and there’s a birthday party in September—the nine-floor luxe building opened to fanfare in the Roaring Twenties and was bankrupt the first time by the Great Depression.
Named to the National Historic Register in 1978, it was bought out of foreclosure in the 1990s and restored by the current owners. Relax in an airy lobby with original Italian tile floor, an English garden, a health spa and Larks Home Kitchen Cuisine, its farm-to-table restaurant and 1920s bar. A ghost might chill on the fifth floor.
Down the block and up a flight of stairs is the circa-1910 Columbia Hotel, with a whimsical rotating art gallery and maybe a spirit or two. New owner and South Africa transplant Jay Bowen also commissioned murals in each guestroom. A traveler lodge, most rooms share bathrooms, and some have bunks, accommodating weary hikers from the nearby Pacific Crest Trail.
During remodeling, she found and removed not-artsy blood-splattered carpets from the 1940s. “There was a lot of blood,” she said.
Weather permitting, book a garden table for dinner at swanky Hearsay. The short ribs are an all-season talker.
Finish dessert in time for a free Green Show, if one is happening. The open-to-everyone performances are staged in a plaza by the Oregon Shakespeare Festival, from midsummer through September.
Then, settle in for one of the festival’s spellbinding plays. Tickets start at $31.
One of Oregon’s best-known draws, the venerable festival teetered following the pandemic and leadership turnover—leading to a statewide bailout plea for millions. Now back on stable footing, the festival offers a slate of outdoor shows until mid-October and indoor performances until later in the month. The nine 2025 productions include the musical Into The Woods, and Shakespeare’s Julius Caesar (with an all-woman cast), As You Like It and Merry Wives of Windsor.
Hungry after the final curtain? Find triangles of cheesy happiness and a college crowd at Creekside Pizza Bistro. At Dangerous Lee’s Local Thirty-One Pub, there’s loud music most days, burgers and gluten-free gumbo, and shirts declaring Ashland a “drinking town with a tourist problem.”
Day 2: HIKING • WINE • SPOOKY WALKING TOURS
The Pacific Crest Trail stretches some 2,650 miles from Mexico to Canada, and it takes five months to walk the entire thing.
For those of us with other things to do, like jobs, snippets of the trail can be enjoyed via several day hikes in the nearby Cascade-Siskiyou National Monument and on Mount Ashland—a city-owned ski area come winter.
First, hike your blood sugar with omelets, crêpes or lemon ricotta-stuffed French toast, which are worth the wait at Morning Glory near campus. Or grab breakfast burritos from Ruby’s, a mainstay in a converted house downtown.
Oregon’s curvy Route 66 has more twists than a Shakespearean comedy. The payoff just thirty minutes from town is the 3-mile Green Springs Mountain Loop, through old growth and savannahs to sweeping valley vistas. National recreation passes are required.
Back downhill, raise a glass to mountain views and hoppy booze at Caldera Brewing, with forty-five beers on tap and a menu that includes seared ahi salad.
If wine is more your (grape) jam, the Rogue Valley’s varied elevations and warm temps help winemakers bottle everything from big Bordeauxs to Burgundians. At Irvine & Roberts Vineyards, chardonnay and pinot noir are the stars—and they’re as impressive as the vaulted tasting room. Also try the pinot-glazed burger.
Sip back in time at Weisinger Family Winery, established in 1988 and one of Oregon’s earliest producers. On the deck, try the fruity Gewürztraminer and the Mescolare red blend, marrying tempranillo, malbec and grenache.
Next up: ghosts. Peter Finkle’s Haunted Ashland walkabouts fill quickly, so book as soon as you know when you’re coming to town. Tours take ninety minutes to two hours.
Reservations also are a must for otherworldly Shrooms Cafe, a casual wellness experience that lets adults try mushroom-derived psilocybin for as little as $25—a huge discount compared to the Willamette Valley. Voters legalized the drug in 2020.
The café offers mellow group sessions, guided meditations, yoga and massage, plus smoothies and snacks (but no mushroom pizza), said lead facilitator Joshua Traphagen. First-time visitors must complete a state-mandated intake process at least twenty-four hours beforehand. The trippy adventures have become a psychedelic tourism draw, attracting visitors from as far away as Japan. Based on the dose, you need to stay at least thirty minutes and as long as six hours afterward, and you can’t drive home.
For dinner, if you feel like an elegant culinary journey, James Beard finalist Josh Dorcak presents a fixed “Cascadian” tasting menu at MÄS, his sixteen-seat restaurant, for $250 per person.
Based on your time and budget, you also can’t go wrong at the frequently recommended Cocorico, where the beet salad, burrata and carbonara are lovely.
Upstairs in the historic town square is the Brickroom, with cocktails and camaraderie until late, and a youth-meets-adulthood surprise on the dessert menu: an affogato with espresso and vanilla ice cream—with chocolate Magic Shell coating.
Day 3: TRAILS • ARTISANS MARKET • PEARS
When you roll out for a morning run or bike spin, be aware: Ashland is only flat on a map. Of course, because it’s Ashland, it’s also OK to be dramatic.
Elevated, you’ll find views and fun trails including a running path along an irrigation canal above campus, and the downhill-only Jabberwocky bike route near Lithia Park.
A flat, paved option heads north along the Bear Creek greenway, which you can take as far as 20 miles to Central Point, north of Medford.
Browse an expansive brunch menu at Greenleaf Restaurant and prowl the weekend Lithia Artisans Market along Ashland Creek, which runs to mid-October.
With so many shows on the Shakespeare festival playbill, there’s probably at least one more you’d like to catch. Matinees are at 1 p.m.
For still-dramatic yet campier fare, the separate Oregon Cabaret Theatre stages musicals and comedies in a converted Ashland church, with optional dining. This fall’s show is Murder for Two, a musical whodunit in which both actors play piano. Their matinees are also at 1 p.m.
Declared Oregon’s official state fruit in 2005, pears date back to the pioneer days of the Rogue Valley, which was once blanketed in orchards. The rise of holiday fruit shipper Harry & David is a product of the popular and prodigious local harvests.
Today, the acreage valleywide is vastly less, but you can still celebrate autumn by the sweet bushel at 50-acre organic Valley View Orchard, where you can pick your own Bartlett, Bosc and Seckel pear varieties. They’ve got buckets, if you don’t. Check their Facebook page to see what’s ripe.
At cozy Osteria La Briccola, marvel at authentic northern Italian fare including seafood and house-made pasta and gnocchi—and also the photo gallery of co-owner Davide Ghizzoni with Hollywood celebrities from his days as a chef in Los Angeles. The Ashland restaurant opened in 2021.
Your final stop is next door at cheery Mix Bakeshop. The owner—one of the daughters of the family that once ran the Oregon-based North’s Chuckwagon buffet chain—serves up almost-too-pretty-to-eat pastries and ice cream.
Also, after several days of adventure, bard and ghost hunting, their Stumptown espresso will help enliven your return trek. And your order? As you like it.
