From Shakespeare to Sarcasm: How Ashland, Oregon, Is Reinventing Its Cultural Identity

By the time Matt Hoffman graduated from high school in his native Ashland, Oregon, he was more than ready to pack his bags and escape the confines of a small town. Looking back at those youthful ambitions, he noted that he simply wanted to spread his wings and experience the wider world. However, after decades away, traveling extensively and building a career, perspective shifted. You travel the world a bit and realize, he reflected, that you grew up in a pretty amazing place.

After spending roughly twenty years in Los Angeles directing commercials, Hoffman ultimately decided to bring his wife and two children back home. He was eager to reconnect with the distinct virtues of the Rogue Valley, from its top-tier schools and expansive outdoor trails to its burgeoning food scene and rich cultural offerings. Yet, upon his return, he found a community facing distinct hurdles. A persistent lack of students had forced local authorities to close two grade schools, and the town’s premier cultural engine, the renowned Oregon Shakespeare Festival, or OSF, had hit a noticeable slump. Combined with a series of increasingly scary regional wildfires, the local area was clearly in need of a revitalization boost.

Hoffman concluded that it might be time for a comprehensive rebrand to spark new energy. Drawing inspiration from nearby Oregon municipalities—where Portland is affectionately known as Stumptown and Eugene proudly wears the title Track Town—he proposed that Ashland could adopt the moniker “Storytown.” This proposed identity serves as a direct nod to the town’s rich theatrical history while simultaneously acting as an open invitation for increased investment and interest in broader comedic and musical arts.

Last year, Hoffman co-founded Storytown Ashland, a newly minted nonprofit organization designed to inject fresh cultural life into the community. The initiative successfully launched the inaugural Ashland Sarcasm Festival, scheduled to take place from December 4 to 6. Following that, the group introduced the Storytown app, a centralized digital calendar intended to track and promote every event happening across the entire valley.

As the recognized cultural capital of the Rogue Valley, Ashland’s traditional offerings remain a massive draw for travelers. Yet, boosters emphasize that these attractions represent only the beginning of what the region serves to visitors. The surrounding area boasts exceptional restaurants, trail networks that easily rival any found across the American West, prime whitewater rafting opportunities, and an ambitious community of winemakers. These vintners are actively taking advantage of a unique Mediterranean climate, experimenting far beyond the traditional Pinot Noirs of the north and the Cabernet Sauvignons of the south. Furthermore, because the valley is situated in the southwest corner of the state—lying more than a four-hour drive south of Portland and nearly a six-hour drive north of San Francisco—it rarely feels overcrowded or overrun by tourists outside of the peak summer months.

The appeal of the local terroir has drawn talent from California’s most famous wine-producing regions. Winemaker Craig Camp made the pivotal move to the valley in 2016, relocating from Napa, California. He was ultimately lured northward by the striking profile of the Siskiyou Mountains and local soils that powerfully reminded him of the landscapes found in Provence or Corsica.

Observing the shifting demographics of visitors, Camp noted that the region is currently receiving a significant influx of travelers from Northern California, who find that the Rogue Valley offers an experience vastly different from what is typically encountered in Napa or Sonoma. Running Troon Vineyard in the Applegate Valley, located just west of Jacksonville, Camp emphasized the personal connection available to guests, explaining that visitors here frequently get the opportunity to meet the actual winemaker and walk the farm, all while soaking in natural beauty that is simply amazing.

Similarly, Dionne Irvine found herself captivated by the region while searching for a new chapter in life. Working as a winemaker alongside her husband, Doug, at Irvine & Roberts Vineyards, she spent time exploring various parts of the state before discovering Ashland. Upon arrival, she recalled thinking that the charming community felt like a living television set, famously remarking that “Mayberry still exists,” referencing the idyllic fictional town from the classic Andy Griffith Show.

As locals deeply invested in the region’s prosperity, Hoffman, Camp, and Irvine frequently find themselves acting as unofficial ambassadors, advising visiting friends, tourists, and clients on the best spots to explore. Their insights are regularly echoed by some of the valley’s most celebrated chefs and prominent hoteliers, who share a curated collection of favorite destinations across local hospitality, dining, outdoor recreation, and cultural sectors.

Hotels

For travelers seeking specialized accommodations, the region offers distinct properties that highlight the natural assets of the valley. Lithia Springs Resort draws visitors primarily for its restorative waters. Located three miles north of downtown Ashland, the resort pipes water straight from its namesake mineral springs directly into the private soaking tubs of 28 distinct bungalows and suites. These accommodations are thoughtfully integrated among serene koi ponds, shaded arbors, and whispering aspen groves, while the on-site Waterstone Spa complements the stay with a comprehensive menu of professional massages and facials.

Dominating the downtown skyline just a single block away from the Oregon Shakespeare Festival theaters stands the Ashland Springs Hotel. Rising nine stories high, this historic 1925 landmark remains an architectural anchor for the community. The property was famously rescued from years of decline and carefully restored in the late 1990s by Doug and Becky Neuman. Today, its ground-floor restaurant, Larks, serves as a longtime favorite gathering spot for diners looking for a reliable meal prior to attending an evening show.

Both the Ashland Springs Hotel and Lithia Springs Resort belong to the Neuman Hotel Group portfolio, where Amanda Owens serves as general manager.

For families and larger groups seeking a different style of accommodation, the Ashland Hills Hotel & Suites offers a convenient base just off Interstate 5. The property features a spacious outdoor pool, tennis courts, and ample acreage. Spanning 14 acres that once comprised the former Windmill Inn, the hotel has been extensively redesigned and updated, featuring striking globe chandeliers, retro ball chairs, and a giant green peace sign prominently displayed in the lobby.

Restaurants

The culinary scene in the Rogue Valley has evolved well beyond standard comfort food, earning national acclaim through innovative dining concepts. At Mŭs, Chef Josh Dorcak operates an intimate 16-seat tasting-menu room that hosts a single seating per night, running Thursday through Sunday. Dorcak applies rigorous Japanese culinary techniques to foraged, hyper-seasonal ingredients sourced directly from the Rogue Valley. The venture originally began as a humble pop-up operating out of a bakery basement, but by 2022, The New York Times had formally recognized it as one of the country’s 50 best restaurants.

For lovers of Italian cuisine, Osteria La Briccola provides a quintessential Ashland dining experience. Diners can secure a deck table suspended directly over Ashland Creek, accessed by walking up a flight of stairs from Calle Guanajuato, and order virtually anything prepared with the kitchen’s house-made pasta. Local regulars consistently swear by the rich gnocchi and the savory wild boar ragu.

Bar Juillet has cultivated a dedicated local following centered around its signature fried chicken. Situated on the Ashland Plaza, this popular neighborhood bar pairs an adventurous selection of natural wines with a vegetable-driven, family-style menu. Doors officially open at four o’clock every afternoon, providing an ideal window for a relaxed dinner before an eight o’clock theater curtain rises.

Operating continuously since 1976, Brothers’ Restaurant remains a staple of the downtown breakfast scene on Main Street. Patrons line up through the weekend to order classic favorites, including the signature cheese blintzes and whatever specialty scone the kitchen has designated as the pastry of the day.

Inside the historic Victorian Winchester Inn, the bar at Alchemy features an impressive wall displaying more than 350 distinct spirits, which bartenders easily access by scaling a sliding library ladder. The establishment’s weekday happy hour, running from four to six o’clock in the afternoon, offers guests seasonal craft cocktails alongside discounted bar bites crafted by the executive chef.

Outdoors

The natural landscape surrounding Ashland offers diverse opportunities for outdoor recreation, ranging from manicured urban green spaces to rugged wilderness canyons. Lithia Park encompasses 93 acres of towering sycamores, reflective ponds, and walking paths that follow the winding course of Ashland Creek upward from the Plaza into the steep canyon. From there, trail networks continue to climb deep into the city’s protected forested watershed. Back down at the Plaza, the public fountains continuously run with the park’s mineral-rich namesake lithia water.

For those seeking elevated panoramic views, Hald-Strawberry Park features two miles of quiet trails situated at the top of Strawberry Lane. The paths wind gently through stands of madrone, manzanita, and ponderosa pine, eventually leading to quiet benches that offer sweeping vistas across the town toward Grizzly Peak. Travelers wishing to access the broader Pacific Crest Trail can take a 30-minute drive up Mount Ashland, where the famous trail intersects with vibrant wildflower meadows while the distant silhouette of Mount Shasta floats across the southern horizon.

Water enthusiasts frequently turn to the Rogue River for world-class whitewater experiences. Congress officially designated the Rogue as one of the nation’s original eight Wild and Scenic Rivers back in 1968. Below Grants Pass, a 40-mile roadless canyon serves as the primary route for multi-day river expeditions. Outfitters such as OARS operate specialized three- to five-day trips that navigate legendary rapids like Rainie Falls and Blossom Bar. For visitors seeking a shorter adventure, Orange Torpedo Trips provides single-day excursions that place participants directly into self-manned inflatable kayaks, locally known as “duckies,” for an up-close and active encounter with the river’s currents.

Culture

Cultural attractions remain the foundational heartbeat of the local economy, anchored by world-class performing arts institutions. The Oregon Shakespeare Festival mounts roughly ten distinct productions each year across three separate performance spaces, most notably the open-air Allen Elizabethan Theatre. The current theatrical season, which runs through late October, pairs classical works such as A Midsummer Night’s Dream and Henry IV, Part One with contemporary stage productions including the hit musical Come From Away.

Building on this theatrical foundation, Amanda Owens highlights the relatively new Ashland Mystery Fest as a major seasonal highlight. Established in 2023 by cozy-mystery author Ellie Alexander—who famously sets her popular Bakeshop Mysteries novel series directly in Ashland—the October festival has rapidly expanded from its primary headquarters in the Historic Ashland Armory into local boutique shops, tea rooms, and the Ashland Springs Hotel.

A short drive away in the neighboring historic town of Jacksonville, the Britt Music & Arts Festival offers a distinct outdoor concert series. Attendees routinely pack blankets and claim spots on the grassy hillside estate once owned by 19th-century photographer Peter Britt. This natural outdoor amphitheater has successfully hosted live summer concert series every year since 1963, welcoming notable musical acts in recent seasons ranging from Bonnie Raitt and Alison Krauss & Union Station to Modest Mouse.