Things To Do
Lithia Park
A beautiful, historic park in the heart of Ashland with winding paths, ponds, and shaded picnic spots. Perfect for a morning stroll or coffee walk.
Main Street and Siskiyou Boulevard
A welcoming, understated stretch filled with local boutiques, cafés, and art galleries. Ideal for shopping, grabbing lunch, or soaking up Ashland’s small-town charm. *Bestow is our favorite local plant and cutesy kitchen knickknacks spot!
Oregon Shakespeare Festival
World-class theater featuring Shakespeare, classic works, and modern plays performed right in downtown Ashland. The Allen Elizabethan Theatre is outdoors and the Angus Bowmer and Thomas Theatres are indoors.
Skout Taphouse & Provisions
A relaxed spot for craft beer, cocktails, and comfort food. Great for a casual hangout with friends or a laid-back evening after exploring town.
Brickroom
A cozy, candle-lit wine and cocktail bar featuring an excellent selection of food and drinks. An easy favorite for relaxed conversation and a low-key night out.
Belle Fiore Winery
A beautiful Tuscan-inspired winery with sweeping views and beautifully manicured grounds. Ideal for wine tasting, photos, and a serene afternoon in the valley.
Grizzly Peak Winery
A scenic winery with great views and approachable wines. Ideal for a relaxed stop with friends or a low-key sunset moment.
