Small City, BIG Tastes: Ashland, Oregon

Photo by Andy Card
When summer rolls around in Ashland, the Oregon Shakespeare Festival is in full swing. The gorgeous Lithia Park trail is busy with people out for a stroll. And there are plenty of places to eat. Even for locals, it can be hard to choose food in Ashland because of the abundance of appetizing options.
Ashland continues to establish itself as a foodie destination in Oregon with its coffee roasters, breweries and restaurants. It even dedicates the month of February to restaurants, calling it Ashland Culinary Month, where chefs prepare special meals, classes and more. When it comes to deciding where to eat in this theatergoers’ city, these establishments are worth checking out.
The best way to start the day is at Case Coffee Roasters ( The local coffee company supplies other coffee shops in the Pacific Northwest with their small- batch roasted beans, but the two locations in Ashland are among the most popular in the city. Enjoy a latte with a house-made syrup and a vegan donut.
Oberon’s Restaurant and Bar ( on N. Main St. hails itself as “the most Ashlandiest spot in Ashland.” The Shakespearean-themed establishment specializes in eccentric, tasty cocktails and pub-style dishes. Owner Andy Card pays special attention to having an ever-changing cocktail menu. His latest creations include a cold brew martini, kumquat sour, Puck’s chamomile old-fashioned and a rum-centric drink called Cheer Thyself. On the food menu, local favorites are the chicken pot pie, the honey bacon apple grilled cheese and an absolutely Medieval giant turkey leg served surrounded by sides.
Also on Main Street is the chic, go-to spot for Italian food. Owners Lisa and Tom Beam changed the restaurant’s look and name to Pie + Vine ( in 2016, but the authentic Italian food and great wine are very much the same. The food is centered around wood-fueled cooking and baking, creating classic and homemade pasta and pizza dishes. Pizza toppings are as simple as a margarita pizza or as fanciful as a beet pie consisting of tri-color beets, goat cheese, orange zest and pumpkin seeds. Another customer favorite is the Rogue piatto, which includes pears, olives, Marcona almonds, gorgonzola and burrata. The wine selection is diverse and Pie + Vine also serves its own label, created by local Weisinger Family Winery.
Another great dinner spot is Alchemy ( on 2nd St. Owner and sommelier Drew Gibbs, along with the rest of his team, vaulted the establishment into the top tier of food and drinks in Ashland back in 2013. Executive Chef Mike Hite has assembled one-of-a-kind flavors for each plate on the dinner menu, separated by first, second and third courses, like beef tartare, grilled romaine and butter-poached lobster garnished with sturgeon caviar. The bistro menu boasts sharable tapas-style plates. The cocktail list is as tempting as the food menu. A favorite is a blueberry tarragon infused Sipsmith gin cocktail called Magenta You’re Turning Me Violet. With more than 200 carefully selected spirits, the drink possibilities are endless. If you’re overwhelmed by the long list, bar manager Kolton Schooley will know how to construct the perfect drink for you.
When you walk into Caldera’s ( warehouse-sized dining room, you’ll see an entire wall filled with working taps. The menu may seem daunting, but it isn’t hard to find the perfect beer for you. Try a hibiscus ginger beer, a chocolate mango sour or a more traditional oatmeal stout. The French fries are crisp, the gourmet salads fresh and the burgers are created with the beer in mind. In Ashland it doesn’t get much better than having a beer at Caldera’s with a white truffle burger in front of you.
Visiting these restaurants is like seeing the tip of an iceberg. There are several more eclectic eateries worth trying. For more information about everything Ashland has to offer, visit