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Ashland, Oregon. Ashland is a city in Jackson County, in the State of Oregon. It lies along Interstate 5 approximately 16 miles (26 km) north of the California border and near the south end of the Rogue Valley. As of 2015, the city's population was approaching 21,000.
What is the driving distance from Ashland Oregon to Portland Oregon? The driving distance between Portland, OR and Ashland, OR is 288 miles.  The driving time would be approximately 4 hours 30 minutes if driving non-stop in good conditions. (â¦The driving time does not take into consideration conditions such as weather, road work and rush hour traffic in urban areas.)