If you plan to come during summer, which is the peak tourist season, be sure to make any necessary car and hotel reservations ahead of time, and be prepared for thicker crowds and more expensive accommodations. Temperatures range from about 80 degrees Fahrenheit down into the 50s at night. In August temperatures may even reach into the high 90s. During the winter, the range is from the mid 40s down to the low 30s, with occasional colder days.

Regardless of Oregon ’s rainy reputation, Ashland gets less than 20 inches of rain per year, plus about 10 inches of snow. Most of the rain falls between October and May, in the form of a light, constant drizzle. Of course some rain falls during the summer as well, so bring the umbrella whenever you come.

If touring the wineries is on your itinerary, keep in mind that most close down during January and February, open on the weekends during the spring and fall, and stay open every day during the summer. And if the Shakespeare Festival is your main draw, you’re in luck. The popular event runs for nine months, from February through October.