Summer in Ashland is the peak tourist season, although it remains a popular place to visit nearly all year round, thanks to the famous Shakespeare Festival. 

If you plan to come during summer, be sure to make any necessary car and hotel reservations ahead of time, and be prepared for busy crowds and more expensive accommodations. Summer temperatures range from about 80º 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. Snow is not common in winter and usually melts in a day under usually sunny skies. However, if driving into Ashland on the I-5, snow can occasionally close or reduce traffic through the Siskiyou Pass north of Mt Shasta and south of Ashland. Chains sometimes required. But in the town, snow is infrequent and brief. There is often good snow at Mt. Ashland where there is a small but good ski lodge and snowboard terrain park. Great for families.

Regardless of Oregon’s rainy reputation, Ashland gets less than 20 inches of rain per year, plus about 8-10 inches of snow. Most of the rain falls between December and May, in the form of light showers or occasional hail. There are occasional thunderstorms during the summer as well, brief and dramatic. 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  Oregon Shakespeare Festival  is your main interest, you’re in luck. The popular event runs for nine months, from February through October. There's more than just Shakepeare with something for everyone. Lots of good restaurants, cafes, shops, boutiques, galleries and the famous Lithia Park, a mile long park downtown, perfect for strolls, hikes, tennis, concerts and picnics.