Ashland sits on Interstate 5, 25 kilometres north of the California border and 480 kilometres south of Portland. Driving is the most practical way to arrive.
By train, Amtrak's Coast Starlight stops at Ashland — one of the more scenic long-distance routes in the United States, running between Los Angeles and Seattle along the Pacific coast. The station is a short cab ride from the centre of town. The schedule is once daily in each direction; northbound in the morning, southbound in the afternoon.
By air, Rogue Valley International–Medford Airport (MFR) is the closest commercial airport, about 25 kilometres north in Medford. It has direct flights to several West Coast cities, though connections through Portland, San Francisco, or Los Angeles are usually required from further afield. Rental cars are available at the airport; the drive to Ashland takes about 20 minutes.
By bus, Greyhound serves Medford; the local Rogue Valley Transportation District (RVTD) runs buses between Medford and Ashland.