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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.
1 Ashland is 14 mi from Jackson County Airport (Medford, OR). 2  Right now, 9 airlines operate out of Jackson County Airport. 3  Jackson County Airport offers nonstop flights to 8 cities.  Every week, at least 238 domestic flights and 0 international flights depart from Jackson County Airport.