Ashland, a small artsy town of about 21,000 in southern Oregon, is famous for its Shakespeare Festival, which runs from March to October. Located near the California border and off Interstate 5, the city, which has a strong New Age and international vibe, now boasts a vibrant and eclectic food scene, with James Beard Award finalists, international restaurants, and a rich cultural scene. The theater festival, which draws theatergoers from many West Coast cities (and will celebrate its 90th anniversary in 2025), and the city’s location, halfway between San Francisco and Portland, Oregon, have influenced the thriving food scene.

“We have a cosmopolitan group of people who come to see plays — about 350,000 each year — who expect and want something different while they’re here, and the city has responded in kind,” says Drew Gibbs, owner of Alchemy and Chateaubriand 36 restaurants and The Winchester Inn, named the nation’s best B&B in August by 10best.. “As a local boy born in 1984, I’ve seen such a boom in restaurants over the last 40 years, from the handful of establishments that were here when my parents opened our inn in 1983.”

Here’s where to eat and drink while visiting.

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This tasting-menu-only restaurant, a finalist for the 2023 and 2024 James Beard Award for Best Chef: Pacific Northwest, offers a parade of 10 to 12 exquisite Japanese-influenced dishes, with a focus on seafood. “I’m so humbled by the support this community has given me,” says Josh Dorcak, a native of Cupertino in the San Francisco Bay Area, who says seeing Tokyo’s micro-restaurants and bars was a life-changing experience that inspired him to open MÄS in 2018 in a small alley. Named one of the country’s 50 best restaurants in 2022 by The New York Times, It serves “Cascadian” cuisine, sourced from Oregon and California, at a six-seat counter and in a small dining room and private library.

The uni (sea urchin) custard with corn dashi topped with grated truffles and trout roe is a standout. So is the halibut flavored with Meyer lemon juice, fermented blueberries, aonori seaweed (which gives it a grassy green tea flavor), and crispy dried fig leaves (which have a slightly coconutty flavor) infused with Thai basil, and a savory macaron infused with Hojicha black tea and filled with foie gras and shiro plum gel. “I like the thrill,” Dorcak says of the bite of guinea fowl stuffed with scallops and truffles, topped with fava beans and chanterelles in a sherry sauce, on my 11-course menu.

Alchemy

Ashland’s first fine-dining restaurant opened in 1983 in the Winchester Inn, a Victorian-style B&B whose main house dates back to 1886. A signature entrée, mushrooms served three ways (flan, sautéed and consommé served tableside), is an “umami flavor bomb,” Gibbs says. Octopus glazed in a housemade XO sauce (which takes 24 hours to prepare), served with basil leaves, cilantro, diced cucumbers and a splash of Vietnamese fish sauce is an unexpected twist on rich, deep flavors. Alchemy, which has Ashland’s largest wine list (more than 500 wines), many from Oregon, is also known for its steaks. (The owners opened a steakhouse across the street.)

Blue Toba

Hailing from the Lake Toba region of Sumatra, chef and owner Birong Hutabarat serves traditional Indonesian cuisine at Blue Toba, which is stylishly and colorfully decorated with shadow puppets, textiles and masks from across the archipelago. “Guy Fieri was blown away when he visited—he’d never had Indonesian food before,” his wife and co-owner, Leslie Caplan, says of the restaurant. Diners, Drive-Ins and Dives The Food Network host shares recipes online for the restaurant’s intensely flavored beef rendang, marinated in 19 spices for five hours (my menu choice), and opor, a candlenut curry.

The cocktails feature Indonesian spices and house-made syrups and tonics, such as the Matahariku, a blend of light rum, orgeat of bancoulier nuts, Giffard banana liqueur with a touch of cognac, orange juice and Blackstrap rum. “We serve artisanal food, artisanal cocktails, everything is artisanal,” says Caplan, who met Hutabarat in Ashland after eight years in Indonesia. “People would come up to me and say, ‘I bought this 40 years ago in Indonesia, I want to give it to you,’” Caplan says of the many items his customers have donated.

Morning Glory

The city’s favorite breakfast spot (hour-long waits are common on weekends) offers creative takes on omelets and crepes and generous portions. The bright blue interior features a painted quote from Japanese haiku master Basho (“I am the one who eats breakfast while contemplating morning glories”). My Alaskan king crab omelet was loaded with crab, artichokes, and scallions in a Parmesan cream, and a bacon-wrapped rockfish crepe wowed me on a previous visit. The salted caramel or lemon ricotta French toast earns rave reviews. Opened in 1997 and ranked the top restaurant in Ashland on Tripadvisor, Morning Glory survived a near-death experience when it closed during the pandemic. But two loyal customers bought it in 2021, retaining the long-standing recipes and staff, and a new owner took over in January 2024.

Chateaubriand 36

The Gibbs family’s French-style steakhouse, which opened in late 2021, offers a variety of steaks, including a 32-ounce Chateaubriand cut for up to four people, duck a l’orange with sweet potato gnocchi, and French onion soup with Tillamook cheddar and Gruyere. Chateaubriand 36 serves wines from France and Oregon, as well as 10 absinthes from France, Oregon, and California. Patio seating offers beautiful views of the Siskiyou Mountains.

Bar Julliet

Crispy fried chicken, honey and Aleppo peppers spiced with Calabrian ranch sauce, served in a heaping bowl for two, are a staple at this Downtown Plaza bistro known for its comfort food classics. Scallops with hazelnuts, yellow beans, tomatoes and spicy fish sauce are another specialty at Bar Juillet, whose newly married owners have roots in San Francisco (chef Wesley Reimer worked at Octavia; Corrie was a manager at Frances) and Portland (Reimer at The Woodsman Tavern).

Oberon

This Plaza bar may resemble a British-style tavern with its Shakespeare play posters and pub food, but it has a serious spirits list with more than 100 Scotch whiskies, including some from Japan and Taiwan, 70 tequilas and a four-page list of bourbons. A “Best Damned List” offers cocktails up to $75, due to rare bottles. Self-proclaimed “Ashland’s most Ashland spot,” Oberon’s Cocktail Bar and Restaurant is popular for live music.

Harana Coffee

Harana, a casual cafe offering modern interpretations of traditional Filipino cuisine, opened in October 2023. Chef/owner Chris Lopez, who worked at Portland’s Urban Farmer at Nines Hotel, opened it with his mother, Teresita. “Working together was a dream of ours, and when this opportunity presented itself, we jumped at it. We wanted to share the beauty and complexity of Filipino cuisine, which is rare in our area.”

My chicken adobo, braised in soy and coconut vinegar with garlic confit, had mushrooms for an umami kick. My pancit miki, a noodle stir-fry, had shrimp and scallops, not the usual chicken or pork, and yakisoba noodles. The lumpia, pork spring rolls, had an extra crunch from water chestnuts. A coconut-milk squash stew with green beans and fermented black beans was outstanding. A Filipina next to me raved about the authentic flavors at Harana, which offers a natural wine list, cocktails and beer.

Green leaf

Local restaurant Greenleaf opened in 1985 on the Plaza with a charming patio overlooking Ashland Creek, serving delicious sandwiches like a blackened chicken BLT with Dijon aioli and avocado and plenty of vegetarian options, like Mediterranean quesadillas and soba bowls. Dish names like Preface, Main Story and Bookends are a nod to Ashland culture.

Belle Fiore Wine Estate

An elegant French chateau-style building with floors bearing hard stone The grounds (colored inlaid stones) are the tasting room at this winery located a 15-minute drive from downtown Ashland. Belle Fiore Estate Winery produces award-winning wines from 17 Italian, French and Spanish varietals, including Barbera, Chardonnay and Montepulciano, from its 31-acre vineyard in the surrounding Rogue Valley AVA. A large upstairs patio, which features live music, offers majestic views of the Siskiyou Mountains. It offers an all-day gourmet menu, as well as pizza and cheese platters.

Weisinger Family Winery

Located a 10-minute drive from downtown Ashland, Weisinger Family Winery was the Rogue Valley’s first winery when it opened in 1988. Its two-story, dog-friendly patio with couches and stunning views of the Siskiyou Mountains is a great place to sample wine, which comes from its own vineyard or from within a five-mile radius. A flight of six wines costs $18.