You may be aware of Oregon’s rainy reputation, but in Ashland, it’s actually not that bad. People in Ashland only see less than 20 inches of rain per year, with most of the rain appearing between December and May. Because of this, they’ll see around 8-10 inches of snow a year, with the rest of the precipitation being light showers and occasionally hail. Thunderstorms are most common in the summer, and while they can be pretty dramatic, they’re fairly brief.
If you’re hoping to go to one of Oregon’s famous, sprawling vineyards and wineries, you’re going to have to take your trip outside of the winter. Most tend to close down during January and February, as well as being open only during weekends during the spring and fall. They’re open every day during the summer, luckily enough.
If you’re coming to Ashland for the Shakespeare Festival, then you hardly need to wait. It runs from February to October, so you can come anytime in between to check things out.