Ashland is our hometown, and we love it! I’m sure you’ll enjoy a visit. Without knowing your interests, I can tell you that we believe the Oregon Shakespeare Festival to be a must-do; this season of high quality plays and performances run nearly year-round and peak in the spring through summer. I recommend seeing at least one play.
Of course, Ashland is also known as a shopping and food scene, so take time to stroll around downtown (all very walkable) and check out the shops and dining venues. I’d be happy to give you specific dining recommendations, but in general, I always recommend Pie + Vine, Caldera Brewing, and Amuse. Lithia Park is located downtown, and is lovely to visit during any time of year. In the winter, an ice skating rink is a centerpiece, and in fall, the changing colors are magnificent. There are hiking trails and single track mountain biking trails connecting the park to a large network of outdoor recreation in the hills above town.What Ashland activities do you recommend?
If you’re wine lovers, the Rogue Valley has several excellent wine trails: I recommend the Applegate Wine Trail and the Upper Rogue Wine Trail. There’s also outdoor recreation just a short drive from town at Hyatt Lake, Howard Prairie Lake, or Lake of the Woods. We also have river rafting on the Rogue. In Ashland, you can book a day trip from Noah’s Rafting, right downtown. I also recommend hiking near Mt. Ashland, where the Pacific Crest Trail can take you right down to Callahan’s Lodge, a wonderful place to stay a few nights. Otherwise, for lodging, I recommend the Ashland Hills Hotel.